Sodium borohydride → HCID 68183278, compound

HRID 513676Notes

Reaction equation

HRID 513676 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[CH3:21])=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>[F: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])=[C:15]([CH3:21])[CH:16]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 68183353HCID 68183353, compound2×

Product 1

HCID 68183278HCID 68183278, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 71, (8-amino-quinolin-7-yl)-(4-fluoro-2-methyl-phenyl)-methanone (Intermediate 380) (200 mg, 0.71 mmol), N-methylsulfamyl chloride (Intermediate 213) (700 mg, 5.4 mmol), NaBH4 (81 mg, 2.14 mmol) and pyridine (6 ml) gave the title compound (40 mg, 16%) after purification by preparative HPLC (neutral conditions).

Sources & evidence

ORD record
ord-934d43554ac84e6a8b9a6a40df95a647
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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