Ammonia → 4-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanamide

HRID 710668노트

반응식

HRID 710668 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:33])[CH:18]([N:23]4[C:27]([CH3:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[N:24]4)[CH2:19][C:20](O)=[O:21])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.N.C[N:36](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:33])[CH:18]([N:23]4[C:27]([CH3:28])=[CH:26][C:25]([C:29]([F:32])([F:30])[F:31])=[N:24]4)[CH2:19][C:20]([NH2:36])=[O:21])[C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867116834-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoic acid

생성물 1

HCID 733360134-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanamide수율 37.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 4-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoic acid (0.029 g, 0.08 mmol) and NH3 (0.3 mL, sat. in CH2Cl2) in DMF (0.6 mL) was added HATU (0.040 g, 0.10 mmol). The mixture was stirred at rt for 30 min. It was then quenched with water. The mixture was partitioned between IPA/CHCl3 (1:2, 50 mL) and sat. NaHCO3 (30 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by reverse phase HPLC to afford the desired product (0.014 g, 37%). 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 7.42 (dd, J=9.2, 4.6 Hz, 2H), 7.16 (dd, J=8.4, 8.0 Hz, 2H), 6.53 (s, 1H), 6.34 (s, 1H), 6.32 (s, 1H), 5.92 (m, 1H), 3.80 (m, 1H), 3.41 (m, 1H), 3.33 (m, 1H), 3.00 (m, 1H), 2.76 (m, 2H), 2.37 (s, 3H), 1.98 (m, 1H), 1.88 (m, 1H); MS: (ES) m/z calculated for C21H20F4N6O2 [M+H]+ 465.1, found 465.1.

후처리

  1. customIt was then quenched with water
  2. customThe mixture was partitioned between IPA/CHCl3 (1:2, 50 mL) and sat. NaHCO3 (30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-7ec8024e89f04a98bae39480ee25b261
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181241B2

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