Water → HCID 89442737, compound

HRID 57133Notes

Reaction equation

HRID 57133 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.Cl.Cl.Cl.Cl.[N:14]1([CH2:18][CH2:19][N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH3:32])[CH:26]=3)[N:22]=[C:21]2[CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[Cs+].[Cs+].O>CS(C)=O>[N:14]1([CH2:18][CH2:19][N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH3:32])[CH:26]=3)[N:22]=[C:21]2[CH:33]2[CH2:34][CH2:35][N:36]([C:7]3[N:6]=[CH:5][N:4]=[C:3]([NH2:9])[C:2]=3[Br:1])[CH2:37][CH2:38]2)[CH2:15][CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 457897135-Bromo-6-chloropyrimidin-4-amineHCID 131736950HCID 131736950, compound

Product 1

HCID 89442737HCID 89442737, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

The reaction mixture of 5-bromo-6-chloro-pyrimidin-4-ylamine (215.00 mg; 1.03 mmol; 1.0 eq.), 4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidine tetrahydrochloride (503.6 mg; 1.03 mmol; 1 eq.), and Cs2CO3 (1344.27 mg; 4.13 mmol; 4 eq.) in DMSO (1.5 ml) was stirred at 120° C. overnight. After cooling, the reaction mixture was poured into water. The precipitate was collected by filtration to yield the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-534531dbb30244ef8bfe6fd13c3762cf
Source dataset
uspto-grants-2016_09
Patent number
US09434714B2

Reaction notes

Loading…