Hexane → HCID 71008528, compound

HRID 1626103Notes

Reaction equation

HRID 1626103 reaction equation
[NH2:1][C@@:2]([C:9]1[CH:10]=[N:11][N:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=2)[CH:13]=1)([CH3:8])[C:3]([F:7])([F:6])[CH2:4][OH:5].C([O-])(=O)C.[Na+].[N:26]#[C:27]Br.CCCCCC>C(O)C.C(OCC)(=O)C>[Br:20][C:16]1[CH:15]=[C:14]([N:12]2[CH:13]=[C:9]([C@:2]([NH2:1])([CH3:8])[C:3]([F:6])([F:7])[CH2:4][O:5][C:27]#[N:26])[CH:10]=[N:11]2)[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 71008948HCID 71008948, compound

Product 1

HCID 71008528HCID 71008528, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A solution of (R)-3-amino-3-[1-(3-bromo-phenyl)-1H-pyrazol-4-yl]-2,2-difluoro-butan-1-ol (5.1 g, 14.73 mmol) and sodium acetate (3.62 g, 44.2 mmol) in ethanol (90 ml) was warmed to 40° C. Cyanogen bromide (1.71 g, 16.21 mmol) was added and the mixture allowed to stir at 40° C. for 16 hours. Removal of the solvent at reduced pressure followed by purification of the resultant crude material by column chromatography on silica gel using a 3:2-mixture of hexane and ethyl acetate as the eluent yielded the (R)-1-[1-(3-bromo-phenyl)-1H-pyrazol-4-yl]-3-cyanato-2,2-difluoro-1-methyl-propylamine (3.2 g, 58% yield) as a colorless sticky solid. MS (ISP): m/z=369.2 [M+H]+.

Workup

  1. customRemoval of the solvent at reduced pressure
  2. customfollowed by purification of the resultant crude material by column chromatography on silica gel using a 3

Sources & evidence

ORD record
ord-c3b21748bf5247ddbe596fc82fc3f107
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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