Phosgene → HCID 25262126, compound

HRID 1894325Notes

Reaction equation

HRID 1894325 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH3:31])[C@:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[NH:11][C:10]([C:21]3[C:22]([O:29][CH3:30])=[N:23][C:24]([O:27][CH3:28])=[N:25][CH:26]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:32](Cl)(Cl)=[O:33].[CH3:36][S:37]([CH2:40][CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)(=[O:39])=[O:38]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH3:31])[C@:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[N:11]([C:32]([N:46]3[CH2:45][CH2:44][N:43]([CH2:42][CH2:41][CH2:40][S:37]([CH3:36])(=[O:38])=[O:39])[CH2:48][CH2:47]3)=[O:33])[C:10]([C:21]3[C:22]([O:29][CH3:30])=[N:23][C:24]([O:27][CH3:28])=[N:25][CH:26]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6371Phosgene3×HCID 498534781-(3-(Methylsulfonyl)propyl)piperazineHCID 68752347HCID 68752347, compound

Product 1

HCID 25262126HCID 25262126, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-2,4-dimethoxy-pyrimidine was converted to the corresponding carbonyl chloride using phosgene and triethylamine in a manner similar to example 2. The carbonyl chloride was then reacted with 4-[3-(methylsulfonyl)propyl]-piperazine (prepared as described in Fotouhi, N. et al. WO 2005110996) following the synthetic procedure as described in example 3 to give the title compound. HR-MS (ES, m/z) calculated for C32H38N6O5SCl2 [(M+H)+] 689.2074, observed 689.2072.

Sources & evidence

ORD record
ord-a2bf58f2d17547539d8e7f6f491694f5
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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