Cesium carbonate → (2S)-1-{[4-Chloro-2-(trifluoromethyl)quinolin-6-yl]methyl}-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one trifluoroacetate

HRID 72381Notes

Reaction equation

HRID 72381 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[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=[C:27]2[Cl:38].[C:39](=[O:42])([O-])[O-:40].[Cs+].[Cs+]>>[F:19][C:18]([F:21])([F:20])[C:39]([OH:40])=[O:42].[Cl:38][C:27]1[C:26]2[C:31](=[CH:32][CH:33]=[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])[CH:25]=2)[N:30]=[C:29]([C:34]([F:37])([F:35])[F:36])[CH:28]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 27363466-(Bromomethyl)-4-chloro-2-(trifluoromethyl)quinolineHCID 136069602(2S)-2-methyl-7-morpholin-4-yl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

Product 1

HCID 86666038(2S)-1-{[4-Chloro-2-(trifluoromethyl)quinolin-6-yl]methyl}-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one trifluoroacetate

Procedure

The product is prepared according to the procedure described in stage k of Example 1, using 95 mg of (2S)-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one (Example 1j) and 101 mg of 6-(bromomethyl)-4-chloro-2-(trifluoromethyl)quinoline, replacing the sodium hydride with 203 g of caesium carbonate. After purification by preparative HPLC/MS (method C), 40 mg of (2S)-1-{[4-chloro-2-(trifluoromethyl)quinolin-6-yl]methyl}-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one, in the form of a trifluoroacetic acid salt, are obtained in the form of a beige powder, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter purification by preparative HPLC/MS (method C), 40 mg of (2S)-1-{[4-chloro-2-(trifluoromethyl)quinolin-6-yl]methyl}-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Sources & evidence

ORD record
ord-4848fee77529438585d22e680a0ee464
Source dataset
uspto-grants-2014_09
Patent number
US08828997B2

Reaction notes

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