Cesium carbonate → Trifluoroacetic acid

HRID 629801Notes

Reaction equation

Cl[C:2]1[C:7]2[O:8][CH2:9][CH2:10][NH:11][C:6]=2[N:5]=[CH:4][N:3]=1.[F:12][C:13]([F:18])([F:17])[C:14]([OH:16])=[O:15].[N:19]1([CH2:23][CH2:24][N:25]2[CH:29]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([C:37]([F:40])([F:39])[F:38])[CH:31]=3)[N:27]=[C:26]2[CH:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[N:19]1([CH2:23][CH2:24][N:25]2[CH:29]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([C:37]([F:40])([F:38])[F:39])[CH:31]=3)[N:27]=[C:26]2[CH:41]2[CH2:42][CH2:43][N:44]([C:2]3[C:7]4[O:8][CH2:9][CH2:10][NH:11][C:6]=4[N:5]=[CH:4][N:3]=3)[CH2:45][CH2:46]2)[CH2:20][CH2:21][CH2:22]1.[C:14]([OH:16])([C:13]([F:18])([F:17])[F:12])=[O:15]

Participants

Conditions

Temperature: 120 °C

Procedure

A reaction mixture of 4-chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine (30.0 mg; 0.17 mmol; 1.0 eq.), 4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate (109.2 mg; 0.17 mmol; 1.0 eq.) and cesium carbonate (227.8 mg; 0.7 mmol; 4.0 eq.) in 1 ml of DMSO was stirred at 120° C. for 48 hrs. The reaction mixture was purified by pre-HPLC to afford the title compound as TFA salt (48.6 mg, 43% yield); LC-MS (M+H=532, obsd.=532);

Workup

customThe reaction mixture was purified by pre-HPLC

Sources & evidence

ORD record: ord-e47ef14d0dad4bb1a8c7ac6dca292ef2
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315517B2

Reaction notes

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