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ノート

反応式

HRID 1159891 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f4d6182889c4e8f99a7bd3e3bbb9138
出典データセット
uspto-grants-2010_10
特許番号
US07812022B2

反応ノート

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