Methanol → HCID 68182945, compound

HRID 513665Notes

Reaction equation

HRID 513665 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=O)=[CH:4][CH:5]=[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+].CO>N1C=CC=CC=1>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[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:24](=[O:26])(=[O:25])[N:23]1[CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 68183153HCID 68183153, compound2×

Product 1

HCID 68182945HCID 68182945, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, (8-amino-quinolin-7-yl)-(2-methoxy-phenyl)-methanone (Intermediate 369) (152 mg, 0.55 mmol), N-methylsulamoyl chloride (Intermediate 213) (212 mg, 1.64 mmol) and NaBH4 (21 mg, 0.55 mmol) in pyridine (10 ml) gave the title compound (85 mg, 44%) after trituration from MeOH.

Sources & evidence

ORD record
ord-3251f0b16526417e968a5770e70e82a1
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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