Chloroacetamide → 2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)acetamide

HRID 531767

反応式

HRID 531767 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[N:22][C:23]([N:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[CH:24][CH:25]=4)[CH:18]=3)[N:13]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:12]=2)[CH:8]=[N:7]1.FC1C=C(C=CC=1)CN1C=C(C2C3C(=NC=C(C4C=NC(N5CCN(C)CC5)=CC=4)C=3)NC=2)C=N1.Cl[CH2:81][C:82]([NH2:84])=[O:83].C(=O)(O)[O-].[Na+]>C(O)C.CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][N:29]([CH2:81][C:82]([NH2:84])=[O:83])[CH2:28][CH2:27]5)=[N:22][CH:21]=4)[CH:18]=3)[N:13]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:12]=2)[CH:8]=[N:7]1

参加物

6

反応物 4

HCID 6580ChloroacetamideHCID 516892Sodium BicarbonateHCID 900303003-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 900309313-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 900312852-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)acetamide収率 73.4%

試薬・触媒・溶媒 1

HCID 21889777Acetone ethanol溶媒

実験手順

Using similar reaction conditions as described in step-i of example-82A, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step 1 compound of example 137) (100 mg, 0.164 mmol) was alkylated using 2-chloroacetamide (23 mg, 0.247 mmol), sodium bicarbonate (42 mg, 0.494 mmol) and ethanol/acetone (3/3 mL) to get 80 mg (73.0%) of the titled compound after purification by column (Silica gel 60/120) chromatography using 5% methanol in dichloromethane as eluent. 1H NMR (CDCl3, 300 MHz): δ 8.60-8.06 (d, 1H), 8.40-8.39 (d, 1H), 8.11-8.08 (d, 2H), 8.00-7.99 (d, 2H), 7.85 (s, 1H), 7.80 (s, 1H), 7.71-7.67 (m, 2H), 7.37-7.33 (m, 2H), 7.06-6.90 (m, 3H), 7.76-7.73 (d, 1H), 5.45 (s, 1H), 5.37 (s, 2H), 3.65-3.62 (t, 4H), 3.09 (s, 1H), 2.71-2.68 (t, 4H), 2.37 (s, 3H).

後処理

  1. customreaction conditions

出典と根拠

ORDレコード
ord-e53a64e4891449b8bb68780c99c9a3b7
出典データセット
uspto-grants-2016_05
特許番号
US09353107B2

関連ノート

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