Diisopropylethylamine → 6-Isopropyl-5'-methyl-N-{(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}-2,2'-bipyridine-4-carboxamide

HRID 1909141노트

반응식

HRID 1909141 반응식
[CH:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([C:17]([OH:19])=O)[CH:5]=1)([CH3:3])[CH3:2].[F:20][C:21]([F:32])([F:31])[C:22]1[N:27]=[CH:26][C:25]([C@H:28]([NH2:30])[CH3:29])=[CH:24][N:23]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([C:17]([NH:30][C@@H:28]([C:25]2[CH:24]=[N:23][C:22]([C:21]([F:32])([F:31])[F:20])=[N:27][CH:26]=2)[CH3:29])=[O:19])[CH:5]=1)([CH3:2])[CH3:3]

참가 물질

6

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 66661534(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethanamineHCID 673383796-Isopropyl-5'-methyl-2,2'-bipyridine-4-carboxylic acid

생성물 1

HCID 461950716-Isopropyl-5'-methyl-N-{(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}-2,2'-bipyridine-4-carboxamide수율 79.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-isopropyl-5′-methyl-2,2′-bipyridine-4-carboxylic acid (25.0 mg, 0.07 mmol) in DMF (0.3 mL) were added hydrochloride salt of (1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethanamine (22.1 mg, 0.08 mmol), HATU (38.2 mg, 0.10 mmol) and diisopropylethylamine (58.5 μL, 0.34 mmol). The mixture was stirred at ambient temperature. After 20 min, the mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (24 mg), HRMS 430.1850 (M+1). 1H NMR (400 MHz, CDCl3): δ 8.96 (s, 2H), 8.48 (s, 1H), 8.43 (d, 8.1 Hz, 1H), 8.37 (s, 1H), 7.67 (d, J=8.2 Hz, 1H), 7.63 (s, 1H), 6.96 (d, J=6.7 Hz, 1H), 5.44-5.35 (m, 1H), 3.24-3.14 (m, 1H), 2.42 (s, 3H), 1.74 (d, J=7.2 Hz, 3H), 1.37 (d, J=6.9 Hz, 6H).

후처리

  1. customthe mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-14d9366fdaa34a11bdb8a1da706a6bba
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598209B2

반응 노트

불러오는 중…