1-Acetylpiperazine → HCID 10128726, compound

HRID 916431Notes

Reaction equation

HRID 916431 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([O:18][C:19]3[C:20]([F:29])=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([CH3:28])=[CH:22]4)=[N:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:30][CH3:31].[C:32]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)(=[O:34])[CH3:33]>CN(C)C=O.C(OCC)(=O)C>[C:32]([N:35]1[CH2:40][CH2:39][N:38]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12]([O:18][C:19]4[C:20]([F:29])=[C:21]5[C:25](=[CH:26][CH:27]=4)[NH:24][C:23]([CH3:28])=[CH:22]5)=[N:13][CH:14]=[N:15]3)=[CH:10][C:9]=2[O:30][CH3:31])[CH2:37][CH2:36]1)(=[O:34])[CH3:33]

Participants

5

Reactant 2

HCID 837951-AcetylpiperazineHCID 58960244HCID 58960244, compound

Product 1

HCID 10128726HCID 10128726, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-[2-(2-bromoethoxy)ethoxy]-6-methoxy-4-(4-fluoro-2-methylindol-5-yloxy)quinazoline (165 mg, 0.38 mmol) and 1-acetylpiperazine (129 mg, 1.01 mmol) in N,N-dimethylformamide (4 ml) was stirred overnight at ambient temperature. The mixture was diluted with ethyl acetate, washed with brine (×2), dried (MgSO4) and concentrated under reduced pressure. Column chromatography of the residue, eluting with 5% 7N ammonia in methanol/methylene chloride gave 7-{2-[2-(4-acetylpiperazin-1-yl)ethoxy]ethoxy}-4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazoline (130 mg, 72%).

Workup

  1. washwashed with brine (×2)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. washColumn chromatography of the residue, eluting with 5% 7N ammonia in methanol/methylene chloride

Sources & evidence

ORD record
ord-8cdbe4f63598496a95227ce71f11d858
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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