Sodium borohydride → HCID 60164656, compound

HRID 513667Notes

Reaction equation

HRID 513667 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([C:14]2[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:24][NH:25][S:26](Cl)(=[O:28])=[O:27].[BH4-].[Na+]>N1C=CC=CC=1>[CH3:24][N:25]1[S:26](=[O:28])(=[O:27])[NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][N:10]=3)[CH:5]=[CH:4][C:3]=2[CH:12]1[C:14]1[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 68183425HCID 68183425, compound2×

Product 1

HCID 60164656HCID 60164656, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, (8-amino-quinolin-7-yl)-(6-trifluoromethyl-pyridin-3-yl)-methanone (Intermediate 371) (100 mg, 0.32 mmol), N-methylsulfamoyl chloride (Intermediate 213) (49 mg, 0.38 mmol) and NaBH4 (12 mg, 0.315 mmol) in pyridine (5 ml) gave the title compound (65 mg, 52%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-ed24384bd89b4425b3df12501a7203e5
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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