Acetyl chloride → HCID 71584841, 화합물

HRID 1257274노트

반응식

HRID 1257274 반응식
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]3[C:17]([Cl:34])=[CH:18][C:19]([F:33])=[C:20]([NH:22][C:23]([NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=4)=[O:24])[CH:21]=3)[C:8](=[O:15])[N:9]2[CH:12]([CH3:14])[CH3:13])=[CH:4][N:3]=1.[C:35](Cl)(=[O:37])[CH3:36]>N1C=CC=CC=1>[Cl:34][C:17]1[CH:18]=[C:19]([F:33])[C:20]([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[O:24])=[CH:21][C:16]=1[C:7]1[C:8](=[O:15])[N:9]([CH:12]([CH3:14])[CH3:13])[C:10]2[C:5]([CH:6]=1)=[CH:4][N:3]=[C:2]([NH:1][C:35](=[O:37])[CH3:36])[CH:11]=2

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 86713691HCID 86713691, 화합물

생성물 1

HCID 71584841HCID 71584841, 화합물수율 85.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of 1-(5-(7-amino-1-isopropyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-chloro-2-fluorophenyl)-3-(3-fluorophenyl)urea (0.07 g, 0.145 mmol) in pyridine (2 mL) was treated with acetyl chloride (0.011 mL, 0.159 mmol) and stirred at RT for 2 h. The mixture was concentrated to dryness, treated with EtOAc, washed with brine, dried over Na2SO4 and concentrated to dryness. The material was treated with Et2O and the solid collected via filtration to afford N-(3-(2-chloro-4-fluoro-5-(3-(3-fluorophenyl)ureido)phenyl)-1-isopropyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)acetamide (65 mg, 84% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.81 (s, 1H), 9.31 (s, 1H), 8.78 (s, 1H), 8.68 (s, 1H), 8.54 (s, 1H), 8.18 (d, J=8.6 Hz, 1H), 7.93 (s, 1H), 7.58 (d, J=11.0 Hz, 1H), 7.46 (dt, J=11.9, 2.3 Hz, 1H), 7.29 (m, 1H), 7.06 (m, 1H), 6.79 (td, J=8.5, 2.6 Hz, 1H), 5.36 (m, 1H), 2.14 (s, 3H), 1.56 (d, J=7.0 Hz, 6H); MS (ESI) m/z: 526.1 [M+H]+.

후처리

  1. concentrationThe mixture was concentrated to dryness
  2. additiontreated with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. additionThe material was treated with Et2O
  7. filtrationthe solid collected via filtration

출처 및 근거

ORD 기록
ord-48d103c057fd4f64a671a1394a4aa8a6
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461179B1

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