Piperidine → HCID 71208726, compound

HRID 1887946Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=1.C(N(CC)C(C)C)(C)C.Cl[C:31]1[CH:36]=[C:35](Cl)[N:34]=[CH:33][N:32]=1.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>CN1C(=O)CCC1>[Cl:14][C:8]1[CH:7]=[C:6]2[C:11]([C:12](=[O:13])[C:3]([CH2:2][NH:1][C:31]3[CH:36]=[C:35]([N:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[N:34]=[CH:33][N:32]=3)=[CH:4][N:5]2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution of 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (30 mg, 0.105 mmol) and N,N-diisopropylethylamine (40.9 mg, 55.2 μL, 0.316 mmol) in NMP (500 μL) was added 4,6-dichloropyrimidine (15.7 mg, 0.105 mmol). The mixture was warmed to 120° C. in a sealed microwave tube. After 1.5 hr, piperidine (35.9 mg, 41.7 μL, 0.421 mmol) was added and heating at 120° C. continued for 9 hr. The reaction mixture was cooled to room temperature. The crude product was purified by preparative reverse-phase HPLC, giving 7-chloro-1-phenyl-3-[(6-piperidin-1-yl-pyrimidin-4-ylamino)-methyl]-1H-quinolin-4-one (25 mg, 53%) as an off-white solid. MS calcd. for C25H24ClN5O [(M+H)+] 446, obsd. 446.

Workup

temperatureheating at 120° C.
waitcontinued for 9 hr
temperatureThe reaction mixture was cooled to room temperature
customThe crude product was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-31f51b77355348b6a5bdfd29dd3fdb4c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

Loading…