Trifluoroacetic acid → 5-Chloro-1H-indole-2-carboxylic acid (1-benzyl-2-oxo-2-piperazin-1-yl-ethyl)-amide

HRID 1872121Notes

Reaction equation

HRID 1872121 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:43])[CH:22]([NH:30][C:31]([C:33]2[NH:34][C:35]3[C:40]([CH:41]=2)=[CH:39][C:38]([Cl:42])=[CH:37][CH:36]=3)=[O:32])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>>[CH2:23]([CH:22]([NH:30][C:31]([C:33]1[NH:34][C:35]2[C:40]([CH:41]=1)=[CH:39][C:38]([Cl:42])=[CH:37][CH:36]=2)=[O:32])[C:21](=[O:43])[N:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15521018HCID 15521018, compound

Product 1

HCID 541903755-Chloro-1H-indole-2-carboxylic acid (1-benzyl-2-oxo-2-piperazin-1-yl-ethyl)-amide

Procedure

Trifluoroacetic acid (4 ml) was added to 4-{2-[(5-chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionyl}-piperazine-1-carboxylic acid tert-butyl ester (0.6 mmol) at 0° C. and the resulting solution was stirred for 0.3 hours and concentrated. The residue was partitioned between ethyl acetate and 2N NaOH, the organic layer separated and washed with brine, dried over Na2SO4, concentrated and the resulting solid triturated with ether: Yield 189 mg, 77%; HPLC (60/40) 2.63 minutes (99%);

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and 2N NaOH
  3. customthe organic layer separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customthe resulting solid triturated with ether
  8. customHPLC (60/40) 2.63 minutes (99%)

Sources & evidence

ORD record
ord-8533c3a6e5e3474ebd12c53b5d5391b1
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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