Sodium borohydride → HCID 68183343, compound

HRID 513671Notes

Reaction equation

HRID 513671 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][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>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][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:15][CH:16]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 68182980HCID 68182980, compound2×

Product 1

HCID 68183343HCID 68183343, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, (8-amino-quinolin-7-yl)-(4-methoxy-phenyl)-methanone (Intermediate 375) (95 mg, 0.34 mmol), N-methylsulfamoyl chloride (Intermediate 213) (133 mg, 1.02 mmol) and NaBH4 (13 mg, 0.34 mmol) in pyridine (5 ml) gave the title compound (8 mg, 7%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-c2b062deeefe4d38a4df8d3ee91a4d0e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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