Acetic Acid → HCID 60164308, compound

HRID 513608Notes

Reaction equation

HRID 513608 reaction equation
N[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[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>[O:12]=[S:10]1(=[O:11])[C:3]2[C:2](=[CH:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=2)[C:15]2[C:14](=[C:23]3[C:18](=[CH:17][CH:16]=2)[CH:19]=[CH:20][CH:21]=[N:22]3)[NH:13]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 68183213HCID 68183213, compound2×

Product 1

HCID 60164308HCID 60164308, compoundYield 4.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-4-cyano-N-quinolin-8-yl-benzenesulfonamide (Intermediate 278) (350 mg, 1.08 mmol), t-butyl nitrite (0.19 ml, 1.62 mmol), AcOH (3.5 ml) and THF (3.5 ml) gave the title compound (15 mg, 4%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-7ceb6ae97dc14a52b465b519bcfe6023
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…