Sodium borohydride → 2-Methyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxide

HRID 513685

Reaction equation

HRID 513685 reaction equation
[NH2:1][C:2]1[C:3]([CH:12]=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:14][NH:15][S:16](Cl)(=[O:18])=[O:17].[BH4-].[Na+]>N1C=CC=CC=1>[CH3:14][N:15]1[S:16](=[O:18])(=[O:17])[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[CH2:12]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 110520988-Aminoquinoline-7-carboxaldehydeHCID 11789235N-Methylsulfamoyl chloride

Product 1

HCID 681832102-Methyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxideYield 14%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, 8-amino-quinoline-7-carbaldehyde (100 mg, 0.58 mmol), N-methylsulfamoyl chloride (226 mg, 1.74 mmol), NaBH4 (22 mg, 0.58 mmol) and pyridine (1 ml) gave the title compound (20 mg, 14%) after purification by column chromatography with heptane/EtOAc (90:10) as the eluent.

Sources & evidence

ORD record
ord-886fe303358d4e579d762fe2c7ef976d
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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