N-methyl-2-pyrrolidone → N-Cyclopropyl-N-[1-(5-cyclopropyl-pyrimidin-2-yl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

HRID 68883Notes

Reaction equation

HRID 68883 reaction equation
Cl.[CH:2]1([N:5]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:6](=[O:18])[C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:17][CH:16]=[N:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:4][CH2:3]1.Cl[C:26]1[N:31]=[CH:30][C:29]([CH:32]2[CH2:34][CH2:33]2)=[CH:28][N:27]=1.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.CN1CCCC1=O>>[CH:2]1([N:5]([CH:19]2[CH2:24][CH2:23][N:22]([C:26]3[N:31]=[CH:30][C:29]([CH:32]4[CH2:34][CH2:33]4)=[CH:28][N:27]=3)[CH2:21][CH2:20]2)[C:6](=[O:18])[C:7]2[CH:8]=[CH:9][C:10]([C:13]3[O:17][CH:16]=[N:15][CH:14]=3)=[CH:11][CH:12]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 468640872-Chloro-5-cyclopropylpyrimidineHCID 68289930N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide hydrochloride

Product 1

HCID 68290561N-Cyclopropyl-N-[1-(5-cyclopropyl-pyrimidin-2-yl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

Conditions

Temperature
70 °C

Procedure

A mixture of N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide hydrochloride (35 mg), 2-chloro-5-cyclopropyl-pyrimidine (46 mg), and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine (82 mg) in N-methylpyrrolidinone (1.5 mol) is stirred at 70° C. overnight. The crude product is purified by preparative HPLC to give the title compound. LC (method 18): tR=1.41 min; Mass spectrum (ESI+): m/z=430 [M+H]+.

Workup

  1. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-9e651429f62d4195bb16b465012fff3f
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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