Ammonium Hydroxide → HCID 86685852, compound

HRID 1629762Notes

Reaction equation

HRID 1629762 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:19]([F:22])([F:21])[F:20])=[CH:9]/[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[NH4+:23].[OH-]>CS(C)=O>[NH2:23][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)([C:19]([F:20])([F:21])[F:22])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 86685853HCID 86685853, compound

Product 1

HCID 86685852HCID 86685852, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a solution of Intermediate 3A (1.53 g, 4.14 mmol) in DMSO (23 mL) was added 15 N aq NH4OH (10 mL). The reaction vessel was sealed and the reaction was stirred at rt for 16 h. Additional DMSO (3 mL) and 15 N aq NH4OH (1 mL) were added and the reaction was stirred at rt for 16 h. Addition of DMSO (4 mL) was repeated and the reaction was stirred for another 16 h. The solution was concentrated in vacuo followed by lyophilization to provide Intermediate 3B (1.8 g, 100%) as a brown oil. LCMS Anal. Calc'd for C17H15BrF3NO 386.21, found [M+H] 388.1.

Workup

  1. customThe reaction vessel was sealed
  2. stirringthe reaction was stirred at rt for 16 h
  3. stirringthe reaction was stirred for another 16 h
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-35d36017edba48519adb182f6c1b086b
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

Loading…