Cesium carbonate → HCID 118290315, compound

HRID 57145Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[CH:9]([CH3:11])[CH3:10].FC(F)(F)C(O)=O.[CH2:19]([O:26][C:27](=[O:55])[N:28]([CH2:53][CH3:54])[CH2:29][CH2:30][N:31]1[CH:35]=[C:34]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[C:38]([C:43]([F:46])([F:45])[F:44])[CH:37]=2)[N:33]=[C:32]1[CH:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[CH2:19]([O:26][C:27](=[O:55])[N:28]([CH2:29][CH2:30][N:31]1[CH:35]=[C:34]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[C:38]([C:43]([F:45])([F:46])[F:44])[CH:37]=2)[N:33]=[C:32]1[CH:47]1[CH2:48][CH2:49][N:50]([C:2]2[C:3]([CH:9]([CH3:11])[CH3:10])=[C:4]([NH2:8])[N:5]=[CH:6][N:7]=2)[CH2:51][CH2:52]1)[CH2:53][CH3:54])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A reaction mixture of 6-chloro-5-isopropyl-pyrimidin-4-ylamine (40.0 mg; 0.23 mmol; 1.0 eq.), ethyl-{2-[4-(4-fluoro-3-trifluoromethyl-phenyl)-2-piperidin-4-yl-imidazol-1-yl]-ethyl}-carbamic acid benzyl ester trifluoroacetate (2) (174.0 mg; 0.23 mmol; 1.0 eq.), and Cs2CO3 (303.7 mg; 0.93 mmol; 4.0 eq.) in DMSO (1.5 ml) was stirred at 120° C. for 48 hr. The crude was purified by prep HPLC to yield the title compound.

Workup

customThe crude was purified by prep HPLC

Sources & evidence

ORD record: ord-4670eb7ef62e4d62912eeb4feea90be6
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434714B2

Reaction notes

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