Cesium carbonate → HCID 89442741, compound

HRID 2284038Notes

Reaction equation

HRID 2284038 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.[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[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=3[CH:9]([CH3:11])[CH3:10])[CH2:45][CH2:46]2)[CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 637282756-Chloro-5-isopropylpyrimidin-4-amineHCID 894427644-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate

Product 1

HCID 89442741HCID 89442741, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A reaction mixture of 6-Chloro-5-isopropyl-pyrimidin-4-ylamine (30.00 mg; 0.17 mmol; 1.00 eq.), 4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate (2) (109.16 mg; 0.17 mmol; 1.00 eq.), and Cs2CO3 (227.81 mg; 0.70 mmol; 4.00 eq.) in DMSO 1.0 ml was stirred at 120° C. for 4 days, purified by prep HPLC, collected title compound 31 mg, yield 27.7%. LC-MS: (M+1=532, obsd.=532).

Workup

  1. custompurified by prep HPLC

Sources & evidence

ORD record
ord-40e3f6fd31194650bca67c699a553227
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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