3-(Cyclopropylamino)propionitrile → 4-((4-((2-Cyanoethyl)(cyclopropyl)amino)-1-fluorocyclohexyl)methoxy)-3-nitrobenzenesulfonamide

HRID 1036057Notes

Reaction equation

HRID 1036057 reaction equation
[F:1][C:2]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:13][C:12]=2[N+:21]([O-:23])=[O:22])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH:24]1([NH:27][CH2:28][CH2:29][C:30]#[N:31])[CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:30]([CH2:29][CH2:28][N:27]([CH:24]1[CH2:26][CH2:25]1)[CH:5]1[CH2:6][CH2:7][C:2]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:13][C:12]=2[N+:21]([O-:23])=[O:22])([F:1])[CH2:3][CH2:4]1)#[N:31]

Participants

5

Reactant 3

HCID 1435373-(Cyclopropylamino)propionitrileHCID 5049666Sodium triacetoxyborohydrideHCID 671267644-((1-Fluoro-4-oxocyclohexyl)methoxy)-3-nitrobenzenesulfonamide

Product 1

HCID 671268274-((4-((2-Cyanoethyl)(cyclopropyl)amino)-1-fluorocyclohexyl)methoxy)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of EXAMPLE 363B (200 mg) in dichloromethane (6 mL) was added 3-(cyclopropylamino)propanenitrile (64 mg) followed by sodium triacetoxyborohydride (184 mg). The mixture was stirred overnight. The reaction mixture was diluted with dichloromethane (400 mL) and washed with 2N aqueous NaOH, water, and brine. After drying over Na2SO4, the mixture was filtered and evaporation of the solvent gave the title compound.

Workup

  1. washwashed with 2N aqueous NaOH, water, and brine
  2. dry with materialAfter drying over Na2SO4
  3. filtrationthe mixture was filtered
  4. customevaporation of the solvent

Sources & evidence

ORD record
ord-2918a31d23f84085b0d85bc8f6aed003
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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