Sodium borohydride → 9-Chloro-1-(4-fluoro-phenyl)-2-methyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxide

HRID 513682Notes

Reaction equation

HRID 513682 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=O)=[CH:4][C:5]([Cl:12])=[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>[Cl:12][C:5]1[C:6]2[C:11]([C:2]3[NH:1][S:24](=[O:26])(=[O:25])[N:23]([CH3:22])[CH:13]([C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=4)[C:3]=3[CH:4]=1)=[N:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chlorideHCID 68183190(8-Amino-5-chloro-quinolin-7-yl)-(4-fluoro-phenyl)-methanone

Product 1

HCID 681832759-Chloro-1-(4-fluoro-phenyl)-2-methyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxideYield 44.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, (8-amino-5-chloro-quinolin-7-yl)-(4-fluoro-phenyl)-methanone 400 (105 mg, 0.34 mmol), N-methylsulfamoyl chloride 213 (135 mg, 1.0 mmol) and NaBH4 (14 mg, 0.34 mmol) in pyridine (4 ml) gave the title compound (57 mg, 44%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-0389697366b54b1b965e55141a317f32
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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