Acetic Acid → HCID 60164546, compound

HRID 513618Notes

Reaction equation

HRID 513618 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[C:10]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3N)(=[O:18])=[O:17])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1)=[O:4].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[C:10]3[C:11](=[CH:12][CH:13]=2)[C:20]2[C:19](=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:16](=[O:18])(=[O:17])[NH:15]3)[N:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 68183293HCID 68183293, compound2×

Product 1

HCID 60164546HCID 60164546, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 8-(2-amino-benzenesulfonylamino)-quinoline-4-carboxylic acid methyl ester (Intermediate 288) (270 mg, 0.75 mmol), t-butyl nitrite (0.14 ml, 1.13 mmol), AcOH (2.7 ml) and THF (2.7 ml) gave the title compound (60 mg, 23%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-53a9a76c7a3246fa86daadce8ddbe9bb
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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