Acetic Acid → HCID 60164545, compound

HRID 513620Notes

Reaction equation

HRID 513620 reaction equation
N[C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([Cl:26])=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)(=[O:14])=[O:13].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[Cl:26][C:19]1[CH:18]=[C:17]2[C:16](=[C:25]3[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]3)[NH:15][S:12](=[O:13])(=[O:14])[C:3]1[C:2]2=[CH:7][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 68183175HCID 68183175, compound2×

Product 1

HCID 60164545HCID 60164545, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-(5-chloro-quinolin-8-yl)-4-methanesulfonyl-benzenesulfonamide (Intermediate 274) (205 mg, 0.5 mmol), t-butyl nitrite (0.09 ml, 0.75 mmol), AcOH (4 ml) and THF (4 ml) gave the title compound (22 mg, 16%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-7edd8da4b89e45d7a077f1dbb8bdb674
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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