Cesium carbonate → (2S)-1-[(5-Chloro-1-benzothiophen-3-yl)methyl]-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 72379Notes

Reaction equation

HRID 72379 reaction equation
[CH3:1][C@@:2]1([C:18]([F:21])([F:20])[F:19])[CH2:17][N:5]2[C:6](=[O:16])[CH:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[N:9]=[C:4]2[NH:3]1.Br[CH2:23][C:24]1[C:28]2[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=2[S:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]2[S:26][CH:25]=[C:24]([CH2:23][N:3]3[C:4]4=[N:9][C:8]([N:10]5[CH2:11][CH2:12][O:13][CH2:14][CH2:15]5)=[CH:7][C:6](=[O:16])[N:5]4[CH2:17][C@@:2]3([CH3:1])[C:18]([F:21])([F:19])[F:20])[C:28]=2[CH:29]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 27798573-(Bromomethyl)-5-chloro-1-benzothiopheneHCID 136069602(2S)-2-methyl-7-morpholin-4-yl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

Product 1

HCID 50899527(2S)-1-[(5-Chloro-1-benzothiophen-3-yl)methyl]-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Procedure

The product is prepared according to the procedure described in stage k of Example 1, using 100 mg of (2S)-2-methyl-7-morpholin-4-yl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one (Example 1j) and 103 mg of 3-(bromomethyl)-5-chloro-1-benzothiophene, replacing the sodium hydride with caesium carbonate. After purification by preparative HPLC/MS (method C), 49 mg of (2S)-1-[(5-chloro-1-benzothiophen-3-yl)methyl]-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one are obtained in the form of a brown solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter purification by preparative HPLC/MS (method C), 49 mg of (2S)-1-[(5-chloro-1-benzothiophen-3-yl)methyl]-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one
  3. customare obtained in the form of a brown solid

Sources & evidence

ORD record
ord-e8d168312fc54faab4b9bd82d818f717
Source dataset
uspto-grants-2014_09
Patent number
US08828997B2

Reaction notes

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