Piperazine → HCID 68905505, compound

HRID 1514110Notes

Reaction equation

HRID 1514110 reaction equation
[CH3:1][C:2]1[C:3]([C:11]2[S:15][C:14]([C:16]([OH:18])=O)=[CH:13][CH:12]=2)=[N:4][O:5][C:6]=1[C:7]([F:10])([F:9])[F:8].[CH3:19][C@H:20]1[CH2:25][NH:24][CH2:23][C@@H:22]([CH3:26])[NH:21]1.C1COCC1.N1CCNCC1>C(N(CC)CC)C>[CH3:19][CH:20]1[NH:21][CH:22]([CH3:26])[CH2:23][N:24]([C:16]([C:14]2[S:15][C:11]([C:3]3[C:2]([CH3:1])=[C:6]([C:7]([F:8])([F:9])[F:10])[O:5][N:4]=3)=[CH:12][CH:13]=2)=[O:18])[CH2:25]1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 8028TetrahydrofuranHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid

Product 1

HCID 68905505HCID 68905505, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and 2,6-cis-dimethylpiperazine by the method described in Example 2 Method B reversing the order of addition such that solid acid chloride was added to a THF solution of triethylamine and piperazine derivative. The reaction mixture was evaporated to an oil and partitioned between EtOAc (5 mL) and water (5 mL). The organic fraction was further washed with brine (2×5 mL), dried over MgSO4, filtered, and evaporated to a colorless solid (79 mg, 85%). 1H NMR (CDCl3) 1.03 (d, J=4.8, 6 H), 1.72-2.20 (m, 1 H), 2.29 (s, 3 H), 2.58 (br, 1 H), 2.78-2.90 (m, 2 H), 4.25 (br, 2 H), 7.24-7.26 (m, 1 H), 7.37-7.39 (m, 1 H). 13C NMR 7.9, 19.4, ˜50 (br obsc), 51.3, 114.7, 118.7 (q, J=271), 128.0, 129.3, 131.2, 140.2, 155.1 (q, J=40), 157.9, 162.4. 19F NMR −63.2. LC/MS 4.43 min, [M+1]+ 374.

Workup

  1. customThe reaction mixture was evaporated to an oil
  2. custompartitioned between EtOAc (5 mL) and water (5 mL)
  3. washThe organic fraction was further washed with brine (2×5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to a colorless solid (79 mg, 85%)
  7. customLC/MS 4.43 min, [M+1]+ 374

Sources & evidence

ORD record
ord-c9b359a766784647b61e95d373d922b9
Source dataset
uspto-grants-2012_07
Patent number
US08222243B2

Reaction notes

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