Acetic Anhydride → HCID 68684870, compound

HRID 2262666Notes

Reaction equation

HRID 2262666 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH:9]=[CH:8][C:7]=1[NH2:19])[CH3:2].[C:21](OC(=O)C)(=[O:23])[CH3:22].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[CH:11]=[C:10]([N:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]2)[CH:9]=[CH:8][C:7]=1[NH:19][C:21](=[O:23])[CH3:22])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68689964HCID 68689964, compound

Product 1

HCID 68684870HCID 68684870, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of [2-Amino-5-(4-methyl-piperazin-1-yl)-phenyl]-acetic acid ethyl ester (438 mg, 1.58 mmol) in CHCl3 (8.0 mL) is added acetic acid anhydride (322 mg, 3.16 mmol) and triethyl amine (240 mg, 2.37 mmol) under argon. The resulting reaction mixture is stirred for 1 h at RT and 1 h at reflux. The reaction mixture is partitioned between CH2Cl2 (25 mL) and water (20 mL) and the layers are separated. The aqueous phase is extracted with CH2Cl2 (2×25 mL) and the combined organic layers are washed with water (2×25 mL), brine (25 mL), dried over Na2SO4 and concentrated at reduced pressure to afford a pale red solid. ES+-MS: 320 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureat reflux
  3. customThe reaction mixture is partitioned between CH2Cl2 (25 mL) and water (20 mL)
  4. customthe layers are separated
  5. extractionThe aqueous phase is extracted with CH2Cl2 (2×25 mL)
  6. washthe combined organic layers are washed with water (2×25 mL), brine (25 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated at reduced pressure
  9. customto afford a pale red solid

Sources & evidence

ORD record
ord-6fd727a675684582ae1fe2289921ca99
Source dataset
uspto-grants-2010_12
Patent number
US07851475B2

Reaction notes

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