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

HRID 651104Notes

Reaction equation

HRID 651104 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 2 N 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 2 N 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-0d08b3b6b37347c3aa1002a3384ebebf
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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