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

HRID 513666Notes

Reaction equation

HRID 513666 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]([C:34]([F:37])([F:36])[F:35])=[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.[CH3:38][NH:39][S:40](Cl)(=[O:42])=[O:41].[BH4-].[Na+]>N1C=CC=CC=1>[CH3:38][N:39]1[S:40](=[O:42])(=[O:41])[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]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 681832377-Chloro-4-methoxyquinolin-8-amineHCID 68183250(8-Amino-quinolin-7-yl)-(4-trifluoromethyl-phenyl)-methanone2×

Product 1

HCID 601646552-Methyl-1-(4-trifluoromethyl-phenyl)-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxideYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure (Intermediate 70), (8-amino-quinolin-7-yl)-(4-trifluoromethyl-phenyl)-methanone (Intermediate 370) (40 mg, 0.13 mmol), N-methylsulamoyl chloride (Intermediate 213) (49 mg, 0.38 mmol) and NaBH4 (4.8 mg, 0.13 mmol) in pyridine (5 ml) gave the title compound (34 mg, 68%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-1e85d9198ec845b1a55a3e2c8d11795a
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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