Methanol → 2-(3-Chlorophenyl)-N-(3-{3-[2-(phenylamino)-4-pyrimidinyl]pyrazolo-[1,5-a]pyridin-2-yl}phenyl)acetamide

HRID 1157543Notes

Reaction equation

HRID 1157543 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.C1N=CN(C(N2C=NC=C2)=O)C=1.[Cl:42][C:43]1[CH:44]=[C:45]([CH2:49][C:50](O)=[O:51])[CH:46]=[CH:47][CH:48]=1.CO>C1COCC1>[Cl:42][C:43]1[CH:44]=[C:45]([CH2:49][C:50]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[C:16]([C:17]4[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[N:18]=4)=[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][N:10]4[N:9]=3)[CH:3]=2)=[O:51])[CH:46]=[CH:47][CH:48]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 158793-Chlorophenylacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 577372234-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamine

Product 1

HCID 686855202-(3-Chlorophenyl)-N-(3-{3-[2-(phenylamino)-4-pyrimidinyl]pyrazolo-[1,5-a]pyridin-2-yl}phenyl)acetamideYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidine (30 mg, 0.08 mmol) (see Example 3, Step H) in THF (3 mL) was added CDI (14 mg, 0.09 mmol). The resultant mixture was stirred at rt for 1 hour. To the mixture was added (3-chlorophenyl)acetic acid (15 mg, 0.09 mmol) and then stirred at rt for 15 h. Methanol (2 mL) was added and the mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel (hexanes/EtOAc) to give the title compound (25 mg, 60% yield). 1H NMR (400 MHz, DMSO-d6): δ 3.68 (s, 2H), 6.53 (d, 1H, J=5.3 Hz), 6.92 (m, 1H), 6.92 (m, 1H), 7.12 (m, 1H), 7.21-7.50 (m, 9H), 7.68-7.76 (m, 3H), 7.89 (m, 1H), 8.26 (d, 1H, J=5.3 Hz), 8.47 (m, 1H), 8.83 (d, 1H, J=6.8 Hz), 9.56 (s, 1H), 10.35 (s, 1H). ES-LC/MS m/z=531 [M+H]+.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on silica gel (hexanes/EtOAc)

Sources & evidence

ORD record
ord-c4b960203377437eadce973393ce6d4a
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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