Tert-Butyl nitrite → HCID 57445040, compound

HRID 227507Notes

Reaction equation

HRID 227507 reaction equation
[C:1]([Cu])#[N:2].N[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([NH2:16])=[O:15])=[C:10]2[S:17]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)(=[O:19])=[O:18].N(OC(C)(C)C)=O>CS(C)=O>[C:1]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([NH2:16])=[O:15])=[C:10]2[S:17]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)(=[O:19])=[O:18])#[N:2]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 100191367-Amino-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamideHCID 178418546HCID 178418546, compound

Product 1

HCID 57445040HCID 57445040, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring suspension of CuCN (35 mg, 0.39 mmol, 1.25 equiv) and 7-Amino-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide (100 mg, 0.31 mmol, 1.0 equiv) in 3 mL of DMSO was added dropwise tert-butyl nitrite (110 μL, 0.92 mmol, 3.0 equiv). After stirring for 18 hours, the title compound was obtained by preparative reversed phase HPLC. Proton NMR for the product was consistent with the titled compound. ESI+MS: 335.3 [M+H]+.

Sources & evidence

ORD record
ord-f3a494b1945b4d458b4eb2387403868a
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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