Diisopropylethylamine → 2-(3-chloropyrazin-2-yl)-N-(2-(3-methoxyphenyl)cyclopropyl)-2-methylpropanamide

HRID 707384노트

반응식

HRID 707384 반응식
[Cl:1][C:2]1[C:3]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]2[CH2:24][CH:23]2[NH2:25])[CH:19]=[CH:20][CH:21]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:8]([CH3:13])([CH3:12])[C:9]([NH:25][CH:23]2[CH2:24][CH:22]2[C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([O:15][CH3:14])[CH:17]=2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 139722362-(3-Methoxyphenyl)cyclopropan-1-amineHCID 866941182-(3-Chloropyrazin-2-yl)-2-methylpropanoic acid

생성물 1

HCID 866942442-(3-chloropyrazin-2-yl)-N-(2-(3-methoxyphenyl)cyclopropyl)-2-methylpropanamide수율 53.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

A mixture of Intermediate 29 (0.2 g, 0.997 mmol), 2-(3-methoxyphenyl)cyclopropanamine (FSSI, mixture of cis/trans, 0.163 g, 0.997 mmol), HATU (GenScript Corporation, 0.455 g, 1.196 mmol), hunig's base (Aldrich, 0.696 ml, 3.99 mmol) in DMF (0.997 ml) and DCM (0.997 ml) was stirred at room temperature overnight. Reaction mixture was diluted with DCM and washed with water and brine. The organic layer was loaded onto a Biotage samplet (25 g). Purification (0-100% EtOAc/hexane) produced 2-(3-chloropyrazin-2-yl)-N-(2-(3-methoxyphenyl)cyclopropyl)-2-methylpropanamide (0.183 g, 0.529 mmol, 53%). M+1: 346.0.

후처리

  1. customReaction mixture
  2. washwashed with water and brine
  3. customPurification (0-100% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-2bfe9631baeb4560a0fa045cd02a9cd3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

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