Acetic Acid → HCID 24858338, compound

HRID 513625Notes

Reaction equation

HRID 513625 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[S:10]([NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2)(=[O:12])=[O:11].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[CH3:9][O:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[C:15]1[C:14](=[C:23]3[C:18](=[CH:17][CH:16]=1)[CH:19]=[CH:20][CH:21]=[N:22]3)[NH:13][S:10]2(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 68183268HCID 68183268, compound2×

Product 1

HCID 24858338HCID 24858338, compoundYield 4.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-5-methoxy-N-quinolin-8-yl-benzenesulfonamide (Intermediate 293) (450 mg, 1.36 mmol), t-butyl nitrite (0.24 ml, 2.04 mmol), AcOH (4.5 ml) and THF (4.5 ml) gave the title compound (19 mg, 4%) after purification by column chromatography with DCM/MeOH (99.7:0.3) as the eluent.

Sources & evidence

ORD record
ord-87dbfb927e4246b5b3fb2c58ad4562dc
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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