Acetic Acid → HCID 67546495, compound

HRID 490627Notes

Reaction equation

HRID 490627 reaction equation
ClC(Cl)(Cl)COC(=O)[N:6]([CH:16]1[CH2:20][CH:19]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]#[N:36])[CH2:25][CH2:24]2)=[O:22])[N:18]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=2[F:45])[CH2:17]1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15].C(O)(=O)C>CO.[Zn]>[F:45][C:39]1[C:40]([F:44])=[CH:41][CH:42]=[CH:43][C:38]=1[CH2:37][N:18]1[CH2:17][CH:16]([NH:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])[CH2:20][CH:19]1[C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]#[N:36])[CH2:25][CH2:24]1)=[O:22]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86625299HCID 86625299, compound

Product 1

HCID 67546495HCID 67546495, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

{1-(2,3-Difluoro-benzyl)-5-[4-(2-cyano-phenyl)-piperazine-1-carbonyl]-pyrrolidin-3-yl}-(2,4-difluoro-benzyl)-carbamic acid 2,2,2-trichloro-ethyl ester (0.13 mmol) and Zn (0.068 g, 1.04 mmol) was dissolved in MeOH (5 ml), and PH was adjust to 5-6 using acetic acid. The mixture was heated to reflux and stirred for 30 min. After removal of methanol, the residue was purified by HPLC to afford final product (5.5 mg, 0.01 mmol) as yellow oil in 8% yield. MS m/e=552.4 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customAfter removal of methanol
  4. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-b51638ad6fa847218038aaa393c500f7
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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