Acetic Anhydride → HCID 46843215, compound

HRID 533732Notes

Reaction equation

HRID 533732 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:20]3[C:19]4[CH2:21][NH:22][CH2:23][CH2:24][C:18]=4[NH:17][C:16]=3[N:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].[C:25](OC(=O)C)(=[O:27])[CH3:26].CCN(C(C)C)C(C)C>O1CCOCC1.CCOC(C)=O.O>[C:25]([N:22]1[CH2:23][CH2:24][C:18]2[NH:17][C:16]3[N:15]=[CH:14][CH:13]=[C:12]([C:9]4[CH:8]=[CH:7][C:6]([S:3]([NH:2][CH3:1])(=[O:5])=[O:4])=[CH:11][CH:10]=4)[C:20]=3[C:19]=2[CH2:21]1)(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 46843214HCID 46843214, compound

Product 1

HCID 46843215HCID 46843215, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 22728543Water ethylacetateSolvent

Procedure

N-Methyl-4-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrol-4-yl)-benzenesulfonamide (75 mg, 0.22 mmol), acetic anhydride (22 mg, 0.22 mmol), and DIEA (0.07 mL, 0.44 mmol) were dissolved in dioxane (2.0 mL), and stirred for 2 h at room temperature. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc, and dried under vacuum to provide 14 (40 mg, 48% yield) as a tan solid. LC-MS (M+H=385, obsd.=385).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with EtOAc
  3. customdried under vacuum

Sources & evidence

ORD record
ord-26ffadb15c904717bff7572f4b623af1
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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