Methanol → HCID 25222719, compound

HRID 1513343Notes

Reaction equation

HRID 1513343 reaction equation
[CH3:1][C:2]1[C:3](=[O:36])[N:4](C(C2C=CC=CC=2)=O)[C:5](=[O:27])[N:6]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][C@H:15]3[C@:13]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=4)([CH2:14]3)[CH2:12]2)[N:7]=1.CO>N>[CH3:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:27])[N:6]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][C@H:15]3[C@:13]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=4)([CH2:14]3)[CH2:12]2)[N:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 59496099HCID 59496099, compound

Product 1

HCID 25222719HCID 25222719, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

6-methyl-4-(phenylcarbonyl)-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 (P4, 102 mg, 0.205 mmol) was dissolved in a 2.0 M solution of ammonia in MeOH (2.046 ml, 4.09 mmol) and the mixture was stirred for 2 hours at rt. Solvent was eliminated under reduced pressure and crude was purified by flash chromatography (eluent DCM to DCM/MeOH/NH3 9:1:0.1) affording the title compound 6-methyl-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 (E1, 67.7 mg, 0.172 mmol).

Workup

  1. customwas purified by flash chromatography (eluent DCM to DCM/MeOH/NH3 9:1:0.1)

Sources & evidence

ORD record
ord-d8cd9a5442f84f4f868cff10e09df018
Source dataset
uspto-grants-2012_07
Patent number
US08217168B2

Reaction notes

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