(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid → 2-[4-chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone

HRID 710616노트

반응식

HRID 710616 반응식
[Cl:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[N:4][N:5]([CH2:8][C:9]([OH:11])=O)[C:6]=1[CH3:7].[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:31]3[CH2:30][CH2:29][CH2:28][NH:27][C:26]=3[CH:25]=[N:24]2)=[CH:19][CH:18]=1>>[Cl:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[N:4][N:5]([CH2:8][C:9]([N:27]2[CH2:28][CH2:29][CH2:30][C:31]3[N:23]([C:20]4[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=4)[N:24]=[CH:25][C:26]2=3)=[O:11])[C:6]=1[CH3:7]

참가 물질

3

반응물 2

HCID 1876853(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acidHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

생성물 1

HCID 733351252-[4-chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone

실험 절차

The compound was prepared from 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method B. The product mixture was washed with 2×1 M NaHSO4 and 2×1.5 M KOH and the organics were eluted through a silica plug. The resulting slurry was concentrated to a white solid that was triturated with 1:1 hexanes:EtOAc to give the title compound as a crystalline white solid (75.9 mg). 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.34 (s, 0.7H), 7.57 (s, 0.3H), 7.44 (m, 2H), 7.15 (m, 2H), 5.24 (s, 0.4H), 5.13 (s, 1.6H), 3.92 (m, 0.5H), 3.84 (m, 1.5H), 2.87 (m, 2H), 2.33 (s, 2.3H), 2.32 (s, 0.7H), 2.12 (m, 1.5H), 2.05 (m, 0.5H); MS: (ES) m/z calculated for C19H17ClF4N5O [M+H]+ 442.1, found 442.0.

후처리

  1. washThe product mixture was washed with 2×1 M NaHSO4 and 2×1.5 M KOH
  2. washthe organics were eluted through a silica plug
  3. concentrationThe resulting slurry was concentrated to a white solid
  4. customthat was triturated with 1:1 hexanes

출처 및 근거

ORD 기록
ord-1e4c46352d3f44de93a90bf3d506379f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181241B2

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