Hydrochloric Acid → 6-(2,4-Dimethyl-1,3-thiazol-5-yl)-2-(3-{(1s,5r)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,4-triazine-3,5(2h,4h)-dione dihydrochloride salt

HRID 1513349Notes

Reaction equation

HRID 1513349 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]2[C:9](=[O:34])[NH:10][C:11](=[O:33])[N:12]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][C@H:21]4[C@:19]([C:23]5[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=5)([CH2:20]4)[CH2:18]3)[N:13]=2)=[C:5]([CH3:7])[N:6]=1.[ClH:35].CO>C(Cl)Cl>[ClH:35].[ClH:35].[CH3:1][C:2]1[S:3][C:4]([C:8]2[C:9](=[O:34])[NH:10][C:11](=[O:33])[N:12]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][C@H:21]4[C@:19]([C:23]5[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:32])[F:31])=[CH:25][CH:24]=5)([CH2:20]4)[CH2:18]3)[N:13]=2)=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 594960976-(2,4-dimethyl-1,3-thiazol-5-yl)-2-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 686536406-(2,4-Dimethyl-1,3-thiazol-5-yl)-2-(3-{(1s,5r)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,4-triazine-3,5(2h,4h)-dione dihydrochloride salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(2,4-dimethyl-1,3-thiazol-5-yl)-2-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,4-triazine-3,5(2H,4H)-dione (E7, 44.3 mg, 0.090 mmol) was dissolved in DCM and treated with HCl 1.25 M in MeOH (2.2 eq) affording after trituration with Et2O 6-(2,4-dimethyl-1,3-thiazol-5-yl)-2-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,4-triazine-3,5(2H,4H)-dione dihydrochloride salt (E8, 41.4 mg, 0.073 mmol).

Sources & evidence

ORD record
ord-dacc2ec7cc1047459a822b78baafab01
Source dataset
uspto-grants-2012_07
Patent number
US08217168B2

Reaction notes

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