Hydrochloric Acid → 5-(6-methyl-2-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione dihydrochloride

HRID 12781Notes

Reaction equation

HRID 12781 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9](=[O:35])[NH:10][C:11](=[O:34])[N:12]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][C@H:22]4[C@:20]([C:24]5[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=5)([CH2:21]4)[CH2:19]3)[CH:13]=2)[CH:5]=[CH:4][CH:3]=1.[ClH:36].O1CCOCC1>>[ClH:36].[ClH:36].[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9](=[O:35])[NH:10][C:11](=[O:34])[N:12]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][C@H:22]4[C@:20]([C:24]5[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:28][CH:29]=5)([CH2:21]4)[CH2:19]3)[CH:13]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 247594455-(6-methyl-2-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 686915305-(6-methyl-2-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione dihydrochlorideYield 31%

Procedure

5-(6-methyl-2-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione was treated with 4N HCl in dioxane (2 eq), to give the title compound as a white powder. (55 mg, 31% yield).

Sources & evidence

ORD record
ord-eb9792bdafca4171954cb8b56dacc7e8
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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