Sodium borohydride → 1-Ethyl-2-methyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxide
Reaction equation
[NH2:1][C:2]1[C:3]([C:12](=O)[CH2:13][CH3:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:16][NH:17][S:18](Cl)(=[O:20])=[O:19].[BH4-].[Na+]>>[CH2:13]([CH:12]1[C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[N:10][CH:9]=[CH:8][CH:7]=3)[C:2]=2[NH:1][S:18](=[O:20])(=[O:19])[N:17]1[CH3:16])[CH3:14]Participants
4
Procedure
In a similar fashion using route 27 general procedure 71, 1-(8-amino-quinolin-7-yl)-propan-1-one 410 (300 mg, 1.6 mmol), N-methylsulfamyl chloride 213 (1 g, 7.7 mmol) and NaBH4 (20 mg, 0.54 mmol) gave the title compound (40 mg, 10%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.
Sources & evidence
- ORD record
- ord-469285c24de3488e9ec6e57cdcb4077b
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102688B2
Reaction notes
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