Triethylamine → 2,2,2-Trifluoro-N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-yl)acetamide

HRID 43025

Reaction equation

HRID 43025 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[CH:16]=[C:15]([CH2:17][OH:18])[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13]3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[F:30][C:31]([F:38])([F:37])[C:32](OCC)=[O:33]>C(Cl)Cl>[F:30][C:31]([F:38])([F:37])[C:32]([NH:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[CH:16]=[C:15]([CH2:17][OH:18])[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13]3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1)=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 58230802(1-((1-Amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

Product 1

HCID 445557322,2,2-Trifluoro-N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-((1-amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol (0.199 mmol, 62.1 mg) and triethylamine (0.399 mmol, 0.056 mL, 40.4 mg) in DCM (1.2 mL) was added a solution of ethyl 2,2,2-trifluoroacetate (0.199 mmol, 0.024 mL, 28.3 mg) and the whole stirred at room temperature for 60 h. The reaction mixture was concentrated under reduced pressure and the residue purified by RP-HPLC to give a clear film (30.0 mg, 0.074 mmol, 36.9%). MS (ESI): m/z [M+H]+ 408.0.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue purified by RP-HPLC
  3. customto give a clear film (30.0 mg, 0.074 mmol, 36.9%)

Sources & evidence

ORD record
ord-6e1b65ccf55a4352b3757c81b5b6f475
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Linked notes

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