Sodium borohydride → HCID 68183453, compound

HRID 513675Notes

Reaction equation

HRID 513675 reaction equation
[CH3:1][NH:2][S:3](Cl)(=[O:5])=[O:4].[NH2:7][C:8]1[C:9]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])=O)=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2.[BH4-].[Na+]>N1C=CC=CC=1>[CH3:29][O:28][C:21]1[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:20]=1[CH:18]1[C:9]2[CH:10]=[CH:11][C:12]3[C:17](=[N:16][CH:15]=[CH:14][CH:13]=3)[C:8]=2[NH:7][S:3](=[O:5])(=[O:4])[N:2]1[CH3:1]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride3×HCID 68183448HCID 68183448, compound2×

Product 1

HCID 68183453HCID 68183453, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-methylsulfamyl chloride (Intermediate 213) (504 mg, 3.88 mmol) was added dropwise to a solution of (8-amino-quinolin-7-yl)-(2,4-dimethoxy-phenyl)-methanone (Intermediate 379) (200 mg, 0.65 mmol) in dry pyridine (10 ml) at 0° C. and the mixture was stirred at room temperature for 36 h (additional equivalents of methylsulfamyl choride were added as required after 24 h). After completion of the reaction (monitored by LCMS), NaBH4 (95 mg, 2.58 mmol) was added and reaction was stirred at room temperature for 18 h. The reaction was quenched with water, concentrated in vacuo and the residue was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (99:1) as the eluent to give the title compound (40 mg, 16%).

Workup

  1. additionwas added
  2. customreaction
  3. stirringwas stirred at room temperature for 18 h
  4. customThe reaction was quenched with water
  5. concentrationconcentrated in vacuo
  6. extractionthe residue was extracted with EtOAc
  7. washThe organic phase was washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by column chromatography with DCM/MeOH (99:1) as the eluent

Sources & evidence

ORD record
ord-106e8d1b00eb4f43a9410e9542a1133f
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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