Cesium carbonate → HCID 71516690, compound

HRID 2284020Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[O:9][CH:10]([CH3:12])[CH3:11].FC(F)(F)C(O)=O.[N:20]1([CH2:24][CH2:25][N:26]2[CH:30]=[C:29]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[C:33]([C:38]([F:41])([F:40])[F:39])[CH:32]=3)[N:28]=[C:27]2[CH:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH2:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[N:20]1([CH2:24][CH2:25][N:26]2[CH:30]=[C:29]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[C:33]([C:38]([F:41])([F:39])[F:40])[CH:32]=3)[N:28]=[C:27]2[CH:42]2[CH2:43][CH2:44][N:45]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=3[O:9][CH:10]([CH3:12])[CH3:11])[CH2:46][CH2:47]2)[CH2:21][CH2:22][CH2:23]1

Participants

Conditions

Temperature: 120 °C

Procedure

A reaction mixture of 6-Chloro-5-isopropoxy-pyrimidin-4-ylamine (40.00 mg; 0.21 mmol; 1.00 eq.), 4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate (2) (133.13 mg; 0.21 mmol; 1.00 eq.), and Cs2CO3 (277.84 mg; 0.85 mmol; 4.00 eq.) in DMSO 5.0 ml was stirred at 120° C. for 2 days, purified the product by HPLC, collected title compound 64 mg, yield 45.5%. LC-MS: (M+1=548, obsd.=548).

Workup

custompurified the product by HPLC

Sources & evidence

ORD record: ord-560c258f95f4458fa89cebb53d32f068
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145392B2

Reaction notes

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