Sodium borohydride → HCID 60163576, compound

HRID 513673Notes

Reaction equation

HRID 513673 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[C:20]([NH2:21])=[C:19]3[C:14]([CH:15]=[CH:16][CH:17]=[N:18]3)=[CH:13][CH:12]=2)=O)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:22][NH:23][S:24](Cl)(=[O:26])=[O:25].[BH4-].[Na+]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:11]3[CH:12]=[CH:13][C:14]4[C:19](=[N:18][CH:17]=[CH:16][CH:15]=4)[C:20]=3[NH:21][S:24](=[O:26])(=[O:25])[N:23]2[CH3:22])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 68183200HCID 68183200, compound2×

Product 1

HCID 60163576HCID 60163576, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, 7-[(3, 4difluorophenyl)carbonyl]-8-aminoquinoline (Intermediate 377) (100 mg, 0.35 mmol), N-methylsulfamoyl chloride (Intermediate 213) (105 mg, 1.0 mmol) and NaBH4 (14 mg, 0.34 mmol) in pyridine (4 ml) gave the title compound (62 mg, 47%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-00ead225f1f04e188f73b5708012d37b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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