Sodium borohydride → HCID 68183395, compound

HRID 513670Notes

Reaction equation

HRID 513670 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:21][NH:22][S:23](Cl)(=[O:25])=[O:24].[BH4-].[Na+]>N1C=CC=CC=1>[F:20][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:23](=[O:25])(=[O:24])[N:22]2[CH3:21])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 68183239HCID 68183239, compound2×

Product 1

HCID 68183395HCID 68183395, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, (8-amino-quinolin-7-yl)-(3-fluoro-phenyl)-methanone (Intermediate 374) (100 mg, 0.38 mmol), N-methylsulfamoyl chloride (Intermediate 213) (146 mg, 1.13 mmol) and NaBH4 (14 mg, 0.38 mmol) in pyridine (3 ml) gave the title compound (50 mg, 39%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-93a73f7152154e8b956f939fa4d30189
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…