Sodium borohydride → HCID 68183038, compound

HRID 513672Notes

Reaction equation

HRID 513672 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([Cl:21])[CH:15]=2)=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:22][NH:23][S:24](Cl)(=[O:26])=[O:25].[BH4-].[Na+]>N1C=CC=CC=1>[Cl:21][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:24](=[O:26])(=[O:25])[N:23]2[CH3:22])[CH:19]=[CH:18][C:17]=1[F:20]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 68183161HCID 68183161, compound2×

Product 1

HCID 68183038HCID 68183038, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, (8-amino-quinolin-7-yl)-(3-chloro-4-fluoro-phenyl)-methanone (Intermediate 376) (80 mg, 0.27 mmol), N-methylsulfamoyl chloride (Intermediate 213) (103 mg, 0.8 mmol) and NaBH4 (10 mg, 0.27 mmol) in pyridine (3 ml) gave the title compound (35 mg, 35%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-d5fb08ec13f546cc9050d5cd1f7a8029
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…