Sodium borohydride → HCID 68183142, compound

HRID 513677Notes

Reaction equation

HRID 513677 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([F:22])[CH:15]=2)=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:23][NH:24][S:25](Cl)(=[O:27])=[O:26].[BH4-].[Na+]>N1C=CC=CC=1>[F:22][C:16]1[CH:15]=[C:14]([CH:12]2[C:3]3[CH:4]=[CH:5][C:6]4[C:11](=[N:10][CH:9]=[CH:8][CH:7]=4)[C:2]=3[NH:1][S:25](=[O:27])(=[O:26])[N:24]2[CH3:23])[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 68183327HCID 68183327, compound2×

Product 1

HCID 68183142HCID 68183142, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 71, (8-amino-quinolin-7-yl)-(3-fluoro-4-methoxy-phenyl)-methanone (Intermediate 381) (200 mg, 0.6 mmol), N-methylsulfamyl chloride (Intermediate 213) (260 mg, 2.0 mmol), NaBH4 (76 mg, 2.0 mmol) and pyridine (2 ml) gave the title compound (130 mg, 52%) after purification by column chromatography with n-hexane/EtOAc (50:50) as the eluent.

Sources & evidence

ORD record
ord-187a9d1bbab24f33a5b5e608927efd8a
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…