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

HRID 513664Notes

Reaction equation

HRID 513664 reaction equation
ClC1C(N)=C2C(C(OC)=CC=N2)=CC=1.[NH2:15][C:16]1[C:17]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)=O)=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2.[CH3:35][NH:36][S:37](Cl)(=[O:39])=[O:38].[BH4-].[Na+]>N1C=CC=CC=1>[CH3:35][N:36]1[S:37](=[O:39])(=[O:38])[NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][N:24]=3)[CH:19]=[CH:18][C:17]=2[CH:26]1[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 681832377-Chloro-4-methoxyquinolin-8-amineHCID 68183254(8-Amino-quinolin-7-yl)-p-tolyl-methanone2×

Product 1

HCID 601646532-Methyl-1-p-tolyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxideYield 5.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure (Intermediate 70), (8-amino-quinolin-7-yl)-p-tolyl-methanone (Intermediate 368) (180 mg, 0.69 mmol), N-methylsulamoyl chloride (Intermediate 213) (267 mg, 2.06 mmol) and NaBH4 (26 mg, 0.69 mmol) in pyridine (10 ml) gave the title compound (12 mg, 5%) after purification by column chromatography with heptane/EtOAc (80:20-50:50) as the eluent.

Sources & evidence

ORD record
ord-4023100d5a46475fb30bb688dfbdd1db
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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