Dichloromethane → HCID 71008464, compound

HRID 1626104Notes

Reaction equation

HRID 1626104 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([C@:13]([NH2:22])([CH3:21])[C:14]([F:20])([F:19])[CH2:15][O:16][C:17]#[N:18])[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[NH4+].ClCCl>CO>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([C@:13]3([CH3:21])[C:14]([F:20])([F:19])[CH2:15][O:16][C:17]([NH2:18])=[N:22]3)[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 71008528HCID 71008528, compound

Product 1

HCID 71008464HCID 71008464, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In a sealed tube a solution of (R)-1-[1-(3-bromo-phenyl)-1H-pyrazol-4-yl]-3-cyanato-2,2-difluoro-1-methylpropylamine (3.0 g, 8.08 mmol) and ammonium hydroxide (25% in water, 7 ml) in methanol (10 ml) was heated to 60° C. for 16 hours. For the workup, the solution was evaporated at reduced pressure. The crude material thus obtained was purified by column chromatography on silica gel using a 95:5-mixture of dichloromethane and methanol as the eluent to give the (R)-4-[1-(3-bromo-phenyl)-1H-pyrazol-4-yl]-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (2.0 g, 54% yield) as a white solid. MS (ISP): m/z=371.2 [M+H]+.

Workup

  1. customFor the workup, the solution was evaporated at reduced pressure
  2. customThe crude material thus obtained
  3. customwas purified by column chromatography on silica gel using a 95

Sources & evidence

ORD record
ord-d3a1b7a9ffb04282b2e523beb2dac9f4
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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