Cesium carbonate → HCID 89442959, compound

HRID 2284039Notes

Reaction equation

HRID 2284039 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[O:9][CH3:10].Cl.[N:12]1([CH2:16][CH2:17][N:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[N:20]=[C:19]2[CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[N:12]1([CH2:16][CH2:17][N:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=3)[N:20]=[C:19]2[CH:33]2[CH2:34][CH2:35][N:36]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=3[O:9][CH3:10])[CH2:37][CH2:38]2)[CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 787216-Chloro-5-methoxypyrimidin-4-amineHCID 89442760HCID 89442760, compound

Product 1

HCID 89442959HCID 89442959, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A reaction mixture of 6-Chloro-5-methoxy-pyrimidin-4-ylamine (45.00 mg; 0.28 mmol; 1.00 eq.), 4-[1-(2-Azetidin-1-yl-ethyl)-2-piperidin-4-yl-1H-imidazol-4-yl]-2-trifluoromethyl-pyridine hydrochloride (4) (148.13 mg; 0.28 mmol; 1.00 eq.), and Cs2CO3 (367.53 mg; 1.13 mmol; 4.00 eq.) in DMSO 1.0 ml was stirred at 120° C. for 2 days, purified by HPLC collected title compound 17 mg. LC-MS: (M+1=503, obsd.=503).

Workup

  1. custompurified by HPLC
  2. customcollected title compound 17 mg

Sources & evidence

ORD record
ord-5a78a27ea432460c813c7fe02d6d6912
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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