1,1'-Carbonyldiimidazole → [1-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexyl]-acetic acid methyl ester

HRID 388456Notes

Reaction equation

HRID 388456 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1([CH2:11][NH:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].N12CCCN=C1CCCCC2>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1([CH2:11][N:12]2[C:13](=[O:21])[C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:20][C:23]2=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68724696{1-[(2-Amino-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester

Product 1

HCID 68728121[1-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexyl]-acetic acid methyl esterYield 99.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {1-[(2-amino-benzoylamino)-methyl]-cyclohexyl}-acetic acid methyl ester (620 mg, 2.04 mmol) and 1,1′-carbonyldiimidazole (660 mg, 4.07 mmol) in THF (25 mL) is added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.6 mL, 4.01 mmol). The mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with EtOAc (100 mL) and is washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate, and is concentrated to afford the desired [1-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexyl]-acetic acid methyl ester (670 mg, 99%).

Workup

  1. washis washed with H2O (50 mL×3)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationis concentrated

Sources & evidence

ORD record
ord-f351c29d370d43d88a5697eda6c80b17
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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