Acetyl chloride → 1-[3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidin-1-yl]ethanone

HRID 872066노트

반응식

HRID 872066 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:11][C@@H:10]2[CH2:12][O:13][C:14]2[C:23]([CH:24]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]3)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][N:20]=3)[N:15]=2)=[N:7][CH:8]=1.[C:30](Cl)(=[O:32])[CH3:31].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:11][C@@H:10]2[CH2:12][O:13][C:14]2[C:23]([CH:24]3[CH2:29][CH2:28][CH2:27][N:26]([C:30](=[O:32])[CH3:31])[CH2:25]3)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][N:20]=3)[N:15]=2)=[N:7][CH:8]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 1176891582-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-3-(piperidin-3-yl)-1,5-naphthyridine

생성물 1

HCID 710858851-[3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidin-1-yl]ethanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-3-(piperidin-3-yl)-1,5-naphthyridine (RR3) (12 mg, 0.03 mmol) in DMF (0.3 mL) was added acetyl chloride (0.006 mL, 0.09 mmol) and Hunig's Base (0.015 mL, 0.09 mmol). After five minutes, the mixture was purified directly by reverse phase chromatography (Waters Sunfire Prep C18 OBD, 5-60% acetonitrile in water with 0.1% TFA modifier) to afford the title compound. 1H NMR (500 MHz, DMSO): δ 8.78 (s, 1 H), 8.13 (s, 3 H), 7.64 (s, 1 H), 7.26 (m, 2 H), 4.50 (m, 2 H), 4.26 (brs, 2 H), 3.77 (s, 3 H), 3.49-3.40 (m, 2 H), 3.08 (m, 2 H), 2.27 (m, 2 H), 2.24-2.19 (m, 1 H), 2.05 (s, 3 H), 1.80 (s, 1 H), 1.23-1.15 (m, 2 H), 1.08 (dt, J=8.7, 4.6 Hz, 1 H); HRMS m/z (M+H) 433.2228 found, 433.2234 required.

후처리

  1. customthe mixture was purified directly by reverse phase chromatography (Waters Sunfire Prep C18 OBD, 5-60% acetonitrile in water with 0.1% TFA modifier)

출처 및 근거

ORD 기록
ord-1c31c67c57b94f77bbd30c8a845978dc
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975261B2

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