Acetic Anhydride → HCID 22477457, compound

HRID 1765601Notes

Reaction equation

HRID 1765601 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[CH:9]=[C:8]2[C:15]1[N:23]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[CH:16]=1)=[NH:4].[C:34](OC(=O)C)(=O)[CH3:35]>C1(C)C=CC=CC=1>[CH3:14][N:10]1[C:11]2[C:7](=[CH:6][C:5]([C:3]3[N:4]=[C:34]([CH3:35])[O:1][N:2]=3)=[CH:13][CH:12]=2)[C:8]([C:15]2[N:23]([S:24]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)(=[O:26])=[O:25])[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[CH:16]=2)=[CH:9]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178427315HCID 178427315, compound

Product 1

HCID 22477457HCID 22477457, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of N-hydroxy-1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indole-5-carboxamidine [0.7 g, Reference Example 26] in toluene (30 mL) at ambient temperature under nitrogen was added acetic anhydride (0.467 g). The reaction mixture was heated at reflux for 4.5 hours then filtered. The filtrate was evaporated to give the title compound (0.32 g) as a dark red oil which was used immediately without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4.5 hours
  3. filtrationthen filtered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d3004bb90f3c49e3a81ffd5b90db5f17
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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