Hydrochloric Acid → 5-(2-methyl-3-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 12777Notes

Reaction equation

[CH3:1][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][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:6][CH:5]=[CH:4][N:3]=1.[ClH:36].O1CCOCC1>>[ClH:36].[ClH:36].[CH3:1][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][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:6][CH:5]=[CH:4][N:3]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 247593415-(2-methyl-3-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 686908255-(2-methyl-3-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione dihydrochlorideYield 36%

Procedure

5-(2-methyl-3-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. (68 mg, 36% yield)

Sources & evidence

ORD record: ord-621c19ee71c44e03a8a1aaa403849fd1
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727988B2

Reaction notes

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