Acetic Acid → HCID 60164307, compound

HRID 513607Notes

Reaction equation

HRID 513607 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:23])(=[O:22])[NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)=[C:6](N)[CH:5]=1.N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]2[C:7]([S:10](=[O:22])(=[O:23])[NH:11][C:12]3[C:13]2=[CH:14][CH:15]=[C:16]2[C:21]=3[N:20]=[CH:19][CH:18]=[CH:17]2)=[CH:6][CH:5]=1)=[O:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 68183010HCID 68183010, compound2×

Product 1

HCID 60164307HCID 60164307, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 3-amino-4-(quinolin-8-ylsulfamoyl)-benzoic acid methyl ester (Intermediate 277) (340 mg, 0.95 mmol), t-butyl nitrite (0.17 ml, 1.4 mmol), AcOH (3.4 ml) and THF (3.4 ml), gave the title compound (60 mg, 18%) after purification by column chromatography with DCM/MeOH (99.8:0.2) as the eluent.

Sources & evidence

ORD record
ord-e8caf5d47bb74941aae9250a8edcea38
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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