Dichloromethane → N-{3-[3-(2-phenylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenyl}-nicotinamide

HRID 1159941ノート

反応式

HRID 1159941 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]=[CH:26][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.C(Cl)Cl.Cl.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[N:37][CH:36]=1>N1C=CC=CC=1>[C:24]1([NH:23][C:19]2[N:18]=[C:17]([C:16]3[C:8]([C:4]4[CH:3]=[C:2]([NH:1][C:34](=[O:41])[C:35]5[CH:40]=[CH:39][CH:38]=[N:37][CH:36]=5)[CH:7]=[CH:6][CH:5]=4)=[N:9][N:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=34)[CH:22]=[CH:21][N:20]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 577372234-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamine

生成物 1

HCID 59513691N-{3-[3-(2-phenylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenyl}-nicotinamide収率 37.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of {4-[2-(3-amino-phenyl)-pyrazolo[1,5-a]pyridin-3-yl]-pyrimidin-2-yl}-phenyl-amine (40 mg, 0.105 mmol) in mixture of DCM (1.2 mL) and pyridine (0.3 mL) was added nicotinoyl chloride hydrochloride (23 mg, 0.11 mmol). The resultant mixture was stirred at rt for 12 h. The resultant precipitate was collected by filtration, and washed with water and diethyl ether to give N-{3-[3-(2-phenylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenyl}-nicotinamide (19 mg). 1H NMR (400 MHz, DMSO-d6) δ 6.56 (m, 1H), 6.95 (m, 1H), 7.15 (m, 1H), 7.27 (m, 2H), 7.36 (m, 1H), 7.51 (m, 2H), 7.62 (m, 1H), 7.71 (m, 2H), 7.96 (m, 1H), 8.11 (m, 1H), 8.17 (m, 1H), 8.35 (m, 1H), 8.50 (m, 1H), 8.79 (m, 1H), 8.86 (m, 1H), 9.13 (m, 1H), 9.64 (s, 1H), 10.6 (s, 1H). LC/MS: m/z 484 (M+1)+.

後処理

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with water and diethyl ether

出典と根拠

ORDレコード
ord-bf5d2b9b7096459b94fb5062b4bb0b1d
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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