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

HRID 1159941Notes

Reaction equation

HRID 1159941 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-bf5d2b9b7096459b94fb5062b4bb0b1d
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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