5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine → 5-[4-[(1,1-Dioxo-1,4-thiazinan-4-yl)methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 472358노트

반응식

HRID 472358 반응식
Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.B([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[CH2:27][CH2:26][S:25](=[O:29])(=[O:28])[CH2:24][CH2:23]2)=[CH:17][CH:16]=1)(O)O>>[O:29]=[S:25]1(=[O:28])[CH2:26][CH2:27][N:22]([CH2:21][C:18]2[CH:19]=[CH:20][C:15]([C:2]3[N:7]4[N:8]=[C:9]([NH2:11])[N:10]=[C:6]4[CH:5]=[CH:4][CH:3]=3)=[CH:16][CH:17]=2)[CH2:23][CH2:24]1

참가 물질

3

반응물 2

HCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amineHCID 54970580(4-((1,1-Dioxidothiomorpholino)methyl)phenyl)boronic acid

생성물 1

HCID 674794405-[4-[(1,1-Dioxo-1,4-thiazinan-4-yl)methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine수율 79.2%

실험 절차

5-{4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}[1,2,4]triazolo[1,5-a]pyridin-2-amine was prepared from 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (368 mg, 1.73 mmol) and 4-[(4-boronophenyl)methyl]-thiomorpholine 1,1-dioxide (0.512 mg, 1.90 mmol), in a manner analogous to Step 73c. The residue was purified on a 12 g Isco silica gel column using a gradient of 0-15% methanol in dichloromethane as an eluent. 5-{4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}[1,2,4]triazolo[1,5-a]pyridin-2-amine (490 mg, 79%) was isolated as a beige foam. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 7.93 (d, J=8.5 Hz, 2H), 7.50 (m, 3H), 7.37 (d, J=7.8 Hz, 1H), 7.07 (d, J=7.8 Hz, 1H), 6.02 (s, 2H), 3.78 (s, 2H), 3.15 (s, 4H), 2.91 (s, 4H). MS=358 (MH)+.

후처리

  1. customThe residue was purified on a 12 g Isco silica gel column

출처 및 근거

ORD 기록
ord-cfbe00f46f1d4efa99848f041ebdeae3
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633173B2

반응 노트

불러오는 중…