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

HRID 12802Notes

Reaction equation

HRID 12802 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([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)[CH:13]=2)=[CH:4][CH:3]=1.[ClH:35]>O1CCOCC1>[ClH:1].[ClH:35].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([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)[CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 247582225-(6-chloro-3-pyridinyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 866159645-(6-chloro-3-pyridinyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione dihydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5-(6-chloro-3-pyridinyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione (E58, 31 mg, 0.06 mmol) was suspended in 1 ml of dioxane and 4M HCl in dioxane solution (31 μl, 0.12 mmol) was added. The mixture was stirred at room temperature for 5 minutes, and then the solvent was removed in vacuum to give 33 mg of the title compound as an off-white powder (94%, yield).

Workup

  1. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-0f105233129d4bc9b399f587cf8d9861
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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