Acetic Anhydride → HCID 68461522, compound

HRID 501199Notes

Reaction equation

HRID 501199 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:36][CH2:35][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]6[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]6)[CH:23]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4].[C:37](OC(=O)C)(=[O:39])[CH3:38]>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:36][CH2:35][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]6[CH2:30][CH2:31][N:32]([C:37](=[O:39])[CH3:38])[CH2:33][CH2:34]6)[CH:23]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 68464494HCID 68464494, compound

Product 1

HCID 68461522HCID 68461522, compoundYield 85.88%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl-2-{8-[3-(piperazin-1-ylmethyl)phenyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (1.5 g, 3.11 mmol) in dry DCM (50 mL) was added 4-dimethylaminopyridine (1.9 g, 15.57 mmol) and then acetic anhydride (0.35 mL, 3.72 mmol) was added at 0° C. and stirred for 5 min. The reaction mass was maintained at room temperature and stirred for 1 h. The progress of the reaction was monitored by TLC, and after completion the reaction mass was diluted with water and extracted with DCM. The DCM layer dried over sodium sulfate and concentrated. The residue was purified by column chromatography to give methyl-2-{8-[3-((4-acetylpiperazin-1-yl)methyl)phenyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (1.4 g, 85.88%) with HPLC purity 99.25%; m/e=525 (M++1).

Workup

  1. stirringstirred for 1 h
  2. extractionextracted with DCM
  3. dry with materialThe DCM layer dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5ba27145a4514b0abee318d816464109
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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