p-Toluenesulfonic acid monohydrate → 2-(3-Acetamido-4-(2-(pyrrolidin-1-yl)ethoxy)phenylamino)-4-(3-fluorobenzylamino)pyrimidine-5-carboxamide

HRID 384263Notes

Reaction equation

N1(O[C:11]2[N:16]=[C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[C:14]([C:26]([NH2:28])=[O:27])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[NH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:40][CH2:41][CH2:42][N:43]2[CH2:47][CH2:46][CH2:45][CH2:44]2)=[C:34]([NH:36][C:37](=[O:39])[CH3:38])[CH:35]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CN1C(=O)CCC1>[C:37]([NH:36][C:34]1[CH:35]=[C:30]([NH:29][C:11]2[N:16]=[C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[C:14]([C:26]([NH2:28])=[O:27])=[CH:13][N:12]=2)[CH:31]=[CH:32][C:33]=1[O:40][CH2:41][CH2:42][N:43]1[CH2:44][CH2:45][CH2:46][CH2:47]1)(=[O:39])[CH3:38]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluorobenzylamino)pyrimidine-5-carboxamide (57 mg, 0.15 mmol) in NMP (0.6 mL) was added N-(5-amino-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamide (47 mg, 0.18 mmol) and pTsOH.H2O (28 mg, 0.15 mmol). The mixture was heated at 100° C. for 2 h, cooled to room temperature, and purified by preparative HPLC to give 2-(3-acetamido-4-(2-(pyrrolidin-1-yl)ethoxy)phenylamino)-4-(3-fluorobenzylamino)pyrimidine-5-carboxamide (46 mg). MS found for C26H30FN7O3 as (M+H)+ 508.5. λ 248.5.

Workup

temperaturecooled to room temperature
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-7cd681af56c9447da5dc5cfd1da82f2e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367689B2

Reaction notes

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