Reference of 20188-40-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 20188-40-3, name is 4-(Aminomethyl)benzamide hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.
Example A85 Preparation of (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-7-{2-[(4- carbamoylbenzyl)amino]-2-oxoethyl}-4-hydroxy-l,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4- dien-l-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl acetate (B266). Step 1. Synthesis of (2S,32)-5- {[(2R,3R,5S,6S)-6- {(2¡ê’,4¡ê’)-5-[(3R,4R,5R,7S)-7-{2-[(4- carbamoylbenzyl)amino]-2-oxoethyl}-4-hydroxy-l,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien- l-yl} -2,5-dimethyltetrahydro-2H-pyran-3-yl]amino} -5-oxopent-3-en-2-yl acetate (B266). To a solution of B1 (18.7 mg, 0.03 mmol, 1 eq.) in NN-dimethylformamide (0.5 mL) at rt was added NN- diisopropylethylamine (21.2 L, 0.12 mmol, 2 eq.) and 4-(aminomethyl)benzamide hydrochloride salt (11.2 mg, 0.06 mmol, 2 eq.), and the reaction was stirred for 1 h. The reaction was purified by by reverse phase chromatography (Method A) to give B266 as a white solid. Yield: 15.4 mg, 0.023 mmol, 77percent. LCMS (Protocol D): m/z 668.37 [M+Na]+, retention time = 0.71 minutes. lB NMR (500 MHz, DMSO-d6) delta 8.50-8.43 (m, 1 H), 7.88 (s, 1 H), 7.82-7.74 (m, 3 H), 7.33-7.25 (m, 3 H), 6.41-6.27 (m, 2 H), 6.10 (d, J= 11.6 Hz, 1 H), 5.87 (dd, J= 11.6 and 7.5 Hz, 1 H), 5.62 (dd, J= 15.8 and 5.5 Hz, 1 H), 5.50-5.43 (m, 1 H), 5.04 (d, J= 5.4 Hz, 1 H), 4.43-4.20 (m, 3 H), 3.68-3.59 (m, 2 H), 3.53-3.45 (m, 1 H), 3.29-3.23 (m, 1 H), 2.78 (d, J= 5.3 Hz, 1 H), 2.68-2.56 (m, 2 H), 2.35-2.13 (m, 3 H), 1.98 (s, 3 H), 1.90-1.72 (m, 4 H), 1.70 (s, 3 H), 1.66-1.58 (m, 1 H), 1.57-1.49 (m, 1 H), 1.25 (d, J= 6.5 Hz, 3 H), 1.04 (d, J= 6.2 Hz, 3 H) , 0.93 (d, J= 7.3 Hz, 3 H).
The chemical industry reduces the impact on the environment during synthesis 4-(Aminomethyl)benzamide hydrochloride. I believe this compound will play a more active role in future production and life.
Reference:
Patent; PFIZER INC.; DIRICO, Kenneth John; EUSTAQUIO, Alessandra S.; GREEN, Michael Eric; HE, Haiyin; HE, Min; KOEHN, Frank Erich; O’DONNELL, Christopher John; PUTHENVEETIL, Sujiet; RATNAYAKE, Anokha Sayani; SUBRAMANYAM, Chakrapani; TESKE, Jesse Alexander; YANG, Hui Yu; WO2014/68443; (2014); A1;,
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