Sodium borohydride → HCID 68183345, compound

HRID 513698Notes

Reaction equation

HRID 513698 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([CH:21]3[O:25][CH2:24][CH2:23][O:22]3)[CH:15]=2)=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:26][NH:27][S:28](Cl)(=[O:30])=[O:29].[BH4-].[Na+]>N1C=CC=CC=1>[O:22]1[CH2:23][CH2:24][O:25][CH:21]1[C:16]1[CH:15]=[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:28](=[O:30])(=[O:29])[N:27]2[CH3:26])[CH:19]=[CH:18][C:17]=1[F:20]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chlorideHCID 68183324HCID 68183324, compound

Product 1

HCID 68183345HCID 68183345, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, (8-amino-quinolin-7-yl)-(3-[1,3]dioxolan-2-yl-4-fluoro-phenyl)-methanone 420 (500 mg, 1.48 mmol), N-methylsulfamoyl chloride 213 (574 mg, 4.43 mmol) and NaBH4 (56 mg, 1.48 mmol) in pyridine (10 ml) gave the title compound (442 mg, 72%) after purification by column chromatography with heptane/EtOAc (50:50) as the eluent.

Sources & evidence

ORD record
ord-d4b883c15c4f4f30915e3b0731159d3d
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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