Cesium carbonate → HCID 89450266, compound

HRID 2284028Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12].FC(F)(F)C(O)=O.[N:22]1([CH2:26][CH2:27][N:28]2[CH:32]=[C:31]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[C:35]([C:40]([F:43])([F:42])[F:41])[CH:34]=3)[N:30]=[C:29]2[CH:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH2:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[N:22]1([CH2:26][CH2:27][N:28]2[CH:32]=[C:31]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[C:35]([C:40]([F:43])([F:41])[F:42])[CH:34]=3)[N:30]=[C:29]2[CH:44]2[CH2:45][CH2:46][N:47]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=3[O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH2:48][CH2:49]2)[CH2:23][CH2:24][CH2:25]1

Participants

Conditions

Temperature: 120 °C

Procedure

A reaction mixture of 6-Chloro-5-(2,2,2-trifluoro-ethoxy)-pyrimidin-4-ylamine (45.00 mg; 0.20 mmol; 1.00 eq.), 4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate (2) (123.48 mg; 0.20 mmol; 1.00 eq.), and Cs2CO3 (257.71 mg; 0.79 mmol; 4.00 eq.) in DMSO 1.0 ml was stirred at 120° C. for 5 days. Purified by HPLC, collected title product 54 mg, yield 39.8%. LC-MS: (M+1=588, obsd.=588).

Workup

customPurified by HPLC

Sources & evidence

ORD record: ord-be3e376fd47a495ba92b029b8f604d0b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145392B2

Reaction notes

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