p-Toluenesulfonic acid → (S)-4-(benzylamino)-2-(3-(1-methylpyrrolidine-2-carboxamido)phenylamino)pyrimidine-5-carboxamide

HRID 533480Notes

Reaction equation

N1(O[C:11]2[N:16]=[C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]([C:25]([NH2:27])=[O:26])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[NH2:28][C:29]1[CH:30]=[C:31]([NH:35][C:36]([C@@H:38]2[CH2:42][CH2:41][CH2:40][N:39]2[CH3:43])=[O:37])[CH:32]=[CH:33][CH:34]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CN1C(=O)CCC1>[CH2:18]([NH:17][C:15]1[C:14]([C:25]([NH2:27])=[O:26])=[CH:13][N:12]=[C:11]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:36]([C@@H:38]3[CH2:42][CH2:41][CH2:40][N:39]3[CH3:43])=[O:37])[CH:30]=2)[N:16]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(benzylamino)pyrimidine-5-carboxamide (50 mg, 0.14 mmol) in NMP (1 mL) was added (S)—N-(3-aminophenyl)-1-methylpyrrolidine-2-carboxamide (33 mg, 0.152 mmol) and pTsOH*H2O (60 mg, 0.28 mmol). The mixture was heated at 100° C. for 2 h, cooled to room temperature, and purified by preparative HPLC to give of (S)-4-(benzylamino)-2-(3-(1-methylpyrrolidine-2-carboxamido)phenylamino)pyrimidine-5-carboxamide (48 mg). MS found for C24H27N7O2 as (M+H)+ 446.5. λ=247.5.

Workup

temperaturecooled to room temperature
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-e02342db53c24f2d9965db098b2534e9
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853230B2

Reaction notes

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