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

HRID 1513353Notes

Reaction equation

HRID 1513353 reaction equation
[F:1][C:2]1[C:7]([C:8]2[C:9](=[O:35])[NH:10][C:11](=[O:34])[N:12]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][C:21]4([C:23]5[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=5)[C:19]([CH3:33])([CH2:20]4)[CH2:18]3)[N:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[ClH:36].CO>C(Cl)Cl>[ClH:36].[ClH:36].[F:1][C:2]1[C:7]([C:8]2[C:9](=[O:35])[NH:10][C:11](=[O:34])[N:12]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][C:21]4([C:23]5[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=5)[C:19]([CH3:33])([CH2:20]4)[CH2:18]3)[N:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 594960956-(2-fluoro-3-pyridinyl)-2-(3-{1-methyl-5-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 866456466-(2-Fluoro-3-pyridinyl)-2-(3-{1-methyl-5-[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-fluoro-3-pyridinyl)-2-(3-{1-methyl-5-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,4-triazine-3,5(2H,4H)-dione (E11, 14 mg, 0.029 mmol) was dissolved in 2 mL of DCM and treated with HCl 1.25M in MeOH (2.2 eq) to form 6-(2-fluoro-3-pyridinyl)-2-(3-{1-methyl-5-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,4-triazine-3,5(2H,4H)-dione dihydrochloride salt (Enantiomer 2) (E12, 15.7 mg, 0.028 mmol).

Sources & evidence

ORD record
ord-0148b03a17b6439d9ae2cf64e3f37162
Source dataset
uspto-grants-2012_07
Patent number
US08217168B2

Reaction notes

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