Ammonium Hydroxide → HCID 71059437, compound

HRID 1525149Notes

Reaction equation

HRID 1525149 reaction equation
[F:1][C:2]([C@:6]1([NH:18][C:19]#[N:20])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[CH2:8][CH2:7]1)([F:5])[CH2:3][OH:4].[OH-].[NH4+]>CO>[F:1][C:2]1([F:5])[CH2:3][O:4][C:19]([NH2:20])=[N:18][C@@:6]21[C:14]1[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=1)[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86674107HCID 86674107, compound

Product 1

HCID 71059437HCID 71059437, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In a tube, a solution of (R)-1-(1,1-difluoro-2-hydroxy-ethyl)-6-nitro-indan-1-yl-cyanamide (1.0 g, 3.55 mmol) in methanol (10 ml) was treated with ammonium hydroxide (25% in water, 3 ml). The tube was sealed and heated at 60° C. for 16 hours. For the workup, the reaction mixture was evaporated at reduced pressure. The crude material was purified by column chromatography (NH-biotage) using a 95:5-mixture of dichloromethane and methanol as the eluent. The (R)-5′,5′-difluoro-6-nitro-2,3,5′,6′-tetrahydrospiro[indene-1,4′-[1,3]oxazin]-2′-amine (500 mg, 50% yield) was obtained as a white solid. MS (ISP): m/z=283.4 [M+H]+.

Workup

  1. customThe tube was sealed
  2. customFor the workup, the reaction mixture was evaporated at reduced pressure
  3. customThe crude material was purified by column chromatography (NH-biotage)

Sources & evidence

ORD record
ord-c7420a2abbe745dbad46f1b3a091c756
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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