Acetic Anhydride → (R)-5-(4-Cyanobenzyl)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid [1-acetyl-4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidin-4-yl]-amide

HRID 1040553Notes

Reaction equation

HRID 1040553 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([NH:10][C:11]([C:13]2([NH:19][C:20]([C:22]3[N:26]4[C@@:27]([CH2:40][C:41]5[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[CH:43][CH:42]=5)([CH3:39])[C:28](=[O:38])[N:29]([C:30]5[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=5)[C:25]4=[N:24][CH:23]=3)=[O:21])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])[CH2:9][CH2:8]1.[C:49](OC(=O)C)(=[O:51])[CH3:50]>N1C=CC=CC=1>[C:49]([N:16]1[CH2:17][CH2:18][C:13]([NH:19][C:20]([C:22]2[N:26]3[C@@:27]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[CH:43][CH:42]=4)([CH3:39])[C:28](=[O:38])[N:29]([C:30]4[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=4)[C:25]3=[N:24][CH:23]=2)=[O:21])([C:11](=[O:12])[NH:10][C:7]2([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:9][CH2:8]2)[CH2:14][CH2:15]1)(=[O:51])[CH3:50]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 58431246(R)-5-(4-cyanobenzyl)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid [4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidin-4-yl]-amide

Product 1

HCID 42632964(R)-5-(4-Cyanobenzyl)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid [1-acetyl-4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidin-4-yl]-amide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (R)-5-(4-cyanobenzyl)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid [4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidin-4-yl]-amide (20 mg, 0.03 mmol) in pyridine (0.5 mL) was added acetic anhydride (0.5 mL). The reaction mixture was stirred at room temperature for 1 h. The solvent was removed in vacuo and the remaining residue was dissolved in water and extracted with CH2Cl2 (3×10 mL). The organic layer was washed with brine and dried over Na2SO4. After removal of the solvent in vacuo, the title compound was obtained as a white solid (21 mg), m/z 725.5 [M+1]+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe remaining residue was dissolved in water
  3. extractionextracted with CH2Cl2 (3×10 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter removal of the solvent in vacuo

Sources & evidence

ORD record
ord-21b87dabba084743b2e0328713d23290
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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