Sodium borohydride → HCID 68183289, compound

HRID 513674Notes

Reaction equation

HRID 513674 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[C:21]([NH2:22])=[C:20]3[C:15]([CH:16]=[CH:17][CH:18]=[N:19]3)=[CH:14][CH:13]=2)=O)=[CH:6][CH:5]=1.[CH3:25][NH:26][S:27](Cl)(=[O:29])=[O:28].[BH4-].[Na+]>N1C=CC=CC=1>[CH3:25][N:26]1[S:27](=[O:29])(=[O:28])[NH:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][N:19]=3)[CH:14]=[CH:13][C:12]=2[CH:10]1[C:7]1[CH:8]=[CH:9][C:4]([O:3][C:2]([F:24])([F:23])[F:1])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 68183172HCID 68183172, compound2×

Product 1

HCID 68183289HCID 68183289, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, 7[(4-trifluoromethoxyphenyl)carbonyl]-8-aminoquinoline (Intermediate 378) (100 mg, 0.31 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 (70 mg, 56%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-3f94d61e59b049949f5e7c3fcabe3b69
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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