Acetic Acid → HCID 60164547, compound

HRID 513622Notes

Reaction equation

HRID 513622 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]=[C:14]([F:22])[CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[F:22][C:14]1[CH:15]=[C:16]2[C:21]([N:20]=[CH:19][CH:18]=[CH:17]2)=[C:12]2[C:13]=1[C:4]1[C:3]([S:8](=[O:10])(=[O:9])[NH:11]2)=[CH:2][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 68183380HCID 68183380, compound2×

Product 1

HCID 60164547HCID 60164547, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-(6-fluoro-quinolin-8-yl)-benzenesulfonamide (Intermediate 290) (200 mg, 0.63 mmol), t-butyl nitrite (0.11 ml, 0.94 mmol), AcOH (2 ml) and THF (2 ml) gave the title compound (35 mg, 19%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-7fcca1bbebbf43ca860fa24d2c215801
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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