Acetic Anhydride → HCID 24894448, compound

HRID 1913399Notes

Reaction equation

HRID 1913399 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[C:11]([CH3:23])=[C:10]([C:24](=[O:27])[CH2:25][CH3:26])[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C1COCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:35]([NH:22][S:19]([C:16]1[CH:15]=[CH:14][C:13]([N:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:9][C:10]([C:24](=[O:27])[CH2:25][CH3:26])=[C:11]2[CH3:23])=[CH:18][CH:17]=1)(=[O:20])=[O:21])(=[O:37])[CH3:36]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23642319A-867744

Product 1

HCID 24894448HCID 24894448, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[5-(4-chloro-phenyl)-2-methyl-3-propionyl-pyrrol-1-yl]-benzenesulfonamide (Example 31, 0.12 g, 0.31 mmol) in dry THF (5 mL) was added triethylamine (0.4 mmol, 0.06 mL) and DMAP (0.031 mmol, 4 mg) at room temperature. 10 Minutes later acetic anhydride (0.62 mmol, 0.06 mL) was added drop wise and the mixture stirred at room temperature for 16 hours. The mixture was diluted with ethyl acetate (100 mL), washed with sodium bicarbonate (saturated solution, 50 mL), water (50 mL) and brine (50 mL). The organic phase was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified over silica using CH2Cl2:MeOH (95:5) as eluant to provide the titled compound. 1H NMR (CDCl3) δ ppm 1.18 (3H), 2.05 (3H), 2.16 (3H), 2.45 (2H), 3.39 (2H), 6.90 (1H), 7.33-7.90 (8H), 8.50 (1H); MS (ESI) m/z 445 (M+H).

Workup

  1. washwashed with sodium bicarbonate (saturated solution, 50 mL), water (50 mL) and brine (50 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified over silica

Sources & evidence

ORD record
ord-35b0a15f4b4b4cb4bdf10f5285003cb4
Source dataset
uspto-grants-2013_12
Patent number
US08609713B2

Reaction notes

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