Imidazole → HCID 67463165, compound

HRID 553836Notes

Reaction equation

HRID 553836 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH2:8]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:46])[C@@H:20]([NH:30][C:31]([C:33]2[CH:38]=[C:37](Cl)[N:36]=[C:35]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:34]=2)=[O:32])[CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:15][CH2:14]1)=[O:12])[CH3:9].O>C1COCC1>[CH2:8]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:46])[C@@H:20]([NH:30][C:31]([C:33]2[CH:38]=[C:37]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[N:36]=[C:35]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:34]=2)=[O:32])[CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:15][CH2:14]1)=[O:12])[CH3:9]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 866224044-{(S)-4-tert-butoxycarbonyl-2-[(6-chloro-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 67463165HCID 67463165, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Imidazole (3 mg) was added to a suspension of NaH (1.7 mg) in anhydrous THF (0.2 ml) at RT. After 30 min stirring at RT, 4-{(S)-4-tert-butoxycarbonyl-2-[(6-chloro-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester (25 mg) dissolved in THF (0.2 ml) was added. The mixture was allowed to stir at RT overnight. Water was added and the resulting mixture was extracted with DCM. The org. phases were dried (Na2SO4) and evaporated off.

Workup

  1. additionwas added
  2. stirringto stir at RT overnight
  3. extractionthe resulting mixture was extracted with DCM
  4. dry with materialphases were dried (Na2SO4)
  5. customevaporated off

Sources & evidence

ORD record
ord-bf707ac3d07642efa973f720dd1573d9
Source dataset
uspto-grants-2011_11
Patent number
US08048881B2

Reaction notes

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