Acetic Acid → HCID 68183346, compound

HRID 513604Notes

Reaction equation

HRID 513604 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:22][CH3:23])=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].C(O)(=O)C.N(OC(C)(C)C)=O>>[CH3:23][O:22][C:15]1[CH:14]=[C:13]2[C:12](=[C:21]3[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]3)[NH:11][S:8](=[O:10])(=[O:9])[C:3]1[C:2]2=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 68183480HCID 68183480, compound2×

Product 1

HCID 68183346HCID 68183346, compoundYield 13.1%

Procedure

In a similar fashion using route 16 general procedure 31, 2-amino-N-(5-methoxyquinolin-8-yl)-benzenesulfonamide (Intermediate 177) (200 mg, 0.61 mmol), acetic acid (36 mg, 0.61 mmol), tert-butyl nitrite (93 mg, 0.91 mmol) gave the title compound (25 mg, 13%) after purification by column chromatography using silica basified by TEA with DCM/MeOH (1:0-499:1) as the eluent.

Sources & evidence

ORD record
ord-2b5ffd1877d64375b5d0a32ae40a5c75
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…