Acetic Acid → HCID 58760945, compound

HRID 1294849Notes

Reaction equation

HRID 1294849 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([O:17][C:18]([C:20]1[N:21]=[C:22]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[N:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[C:24]=1[CH2:25][CH:26]=O)=[O:19])[CH3:16].[CH:42]1([NH2:47])[CH2:46][CH2:45][CH2:44][CH2:43]1.C(O)(=O)C>ClCCCl>[CH2:15]([O:17][C:18]([C:20]1[N:21]=[C:22]([C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)[N:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[C:24]=1[CH2:25][CH2:26][NH:47][CH:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1)=[O:19])[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2906CyclopentylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58760944HCID 58760944, compound

Product 1

HCID 58760945HCID 58760945, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (32 mg, 0.152 mmol) was added to a solution of 2-(4-chloro-phenyl)-1-(2-chloro-phenyl)-5-(2-oxo-ethyl)-1H-imidazole-4-carboxylic acid ethyl ester I-5h (34 mg, 0.084 mmol), cyclopentylamine (12 μl, 0.118 mmol), and acetic acid (5 μl, 0.09 mmol) in 1,2-dichlorethane (2 ml) at room temperature. The reaction mixture was quenched with 1N NaOH and extracted with CH2Cl2 (3×). The combined CH2Cl2 extracts were washed with sat'd aq NaCl, dried, and concentrated in vacuo. The crude residue was purified on a 1 mm chromatotron plate using 100% EtOAc to give I-5i as a colorless oil (22 mg): +APCI MS (M+1) 472.2.

Workup

  1. customThe reaction mixture was quenched with 1N NaOH
  2. extractionextracted with CH2Cl2 (3×)
  3. washThe combined CH2Cl2 extracts were washed with sat'd aq NaCl
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on a 1 mm chromatotron plate

Sources & evidence

ORD record
ord-29fcbf197145480e848d14547e6785f1
Source dataset
uspto-grants-2007_07
Patent number
US07241788B2

Reaction notes

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