2-Chloro-6-fluorobenzoyl chloride → 2-Chloro-6-fluoro-N-[3-(3-{2-[(3-fluorophenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]benzamide

HRID 1159891

반응식

HRID 1159891 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:31][C:32]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:33]=1[C:34](Cl)=[O:35]>C1COCC1>[Cl:31][C:32]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:33]=1[C:34]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:3]=1)=[O:35]

참가 물질

4

반응물 2

HCID 27365472-Chloro-6-fluorobenzoyl chlorideHCID 595114034-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-fluorophenyl)-2-pyrimidinamine

생성물 1

HCID 595138072-Chloro-6-fluoro-N-[3-(3-{2-[(3-fluorophenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]benzamide수율 65%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-fluorophenyl)-2-pyrimidinamine (92 mg, 0.23 mmol) in 2 mL of THF, added 2-chloro-6-fluorobenzoyl chloride (48 mg, 0.27 mmol). The reaction was stirred for 30 min at rt and quenched by addition of polystyrene-trisamine resin (20 mg). The reaction was allowed to stir overnight. The reaction was treated with excess Et3N, filtered, and washed with THF. The filtrate was collected, reduced in vacuo, and upon treatment with DCM, a white solid formed. Filtration and washing with the solid with Et2O yielded the desired product as a white solid, 96 mg, 65% yield. 1H NMR (400 MHz, d6-DMSO): δ 10.89 (s, 1H); 9.78 (s, 1H); 8.84 (d, J=6 Hz, 1H); 8.30 (d, J=5 Hz, 1H); 8.00 (s, 1H); 7.77-7.23 (m, 2H); 7.55-7.33 (m, 7H); 7.22 (q, J=8 Hz, 1H); 7.11 (t, J=7 Hz, 1H); 6.69 (td, J=2, 8 Hz, 1H); 6.60 (d, J=5 Hz, 1H). HRMS calculated C30H20ClF2N6O [M+H]+ 553.1355, found 553.1360.

후처리

  1. customquenched by addition of polystyrene-trisamine resin (20 mg)
  2. stirringto stir overnight
  3. additionThe reaction was treated with excess Et3N
  4. filtrationfiltered
  5. washwashed with THF
  6. customThe filtrate was collected
  7. customupon treatment with DCM, a white solid formed
  8. filtrationFiltration
  9. washwashing with the solid with Et2O

출처 및 근거

ORD 기록
ord-9f4d6182889c4e8f99a7bd3e3bbb9138
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812022B2

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