Sodium borohydride → methyl N-[[2-chloro-5-[1-(3,4-dihydro-3-hydroxy-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate

HRID 1408435Notes

Reaction equation

HRID 1408435 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:14]=[CH:15][C:16]4[O:21][CH2:20][C:19](=[O:22])[CH2:18][C:17]=4[CH:23]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:24][NH:25][C:26](=[O:29])[O:27][CH3:28].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:14]=[CH:15][C:16]4[O:21][CH2:20][CH:19]([OH:22])[CH2:18][C:17]=4[CH:23]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:24][NH:25][C:26](=[O:29])[O:27][CH3:28]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67151129methyl N-[[2-chloro-5-[1-(3,4-dihydro-3-oxo-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate2×

Product 1

HCID 67151126methyl N-[[2-chloro-5-[1-(3,4-dihydro-3-hydroxy-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamateYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl N-[[2-chloro-5-[1-(3,4-dihydro-3-oxo-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate (i.e. the product of Example 10) (100 mg, 0.24 mmol) in methanol (10 mL) was added sodium borohydride (19 mg, 0.48 mmol) and the reaction mixture was stirred at ambient temperature for 1 hour. After TLC analysis (30% ethyl acetate/pet ether) showed completion of reaction, the solvent was concentrated under vacuum. The crude residue was cooled to 0° C. and acidified with 1N HCl. The aqueous mixture was extracted three times with ethyl acetate. The combined the organic phases were washed with water, brine and dried over Na2SO4. The solvent was concentrated under vacuum to give the title compound, a compound of the present invention, (60 mg, 60% yield) as a solid.

Workup

  1. customcompletion of reaction
  2. concentrationthe solvent was concentrated under vacuum
  3. temperatureThe crude residue was cooled to 0° C.
  4. extractionThe aqueous mixture was extracted three times with ethyl acetate
  5. washwere washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe solvent was concentrated under vacuum

Sources & evidence

ORD record
ord-02508aefbdad4643bc08ce3c65bd40da
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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