Acetic Acid → HCID 68183025, compound

HRID 513619Notes

Reaction equation

HRID 513619 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:17]2[N:18]=[CH:19][S:20][C:16]=2[CH:15]=[CH:14][CH:13]=1)(=[O:10])=[O:9].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[CH:5]1[C:4]2[C:13]3[C:12](=[C:17]4[C:16](=[CH:15][CH:14]=3)[S:20][CH:19]=[N:18]4)[NH:11][S:8](=[O:10])(=[O:9])[C:3]=2[CH:2]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 68183255HCID 68183255, compound2×

Product 1

HCID 68183025HCID 68183025, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-benzothiazol-4-yl-benzenesulfonamide (Intermediate 289) (190 mg, 0.62 mmol), t-butyl nitrite (96 mg, 0.93 mmol), AcOH (1.9 ml) and THF (4 ml) gave the title compound (35 mg, 19.5%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-5fc1811b99be48bb9140f9f571833617
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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