Diisopropylethylamine → HCID 45274309, compound

HRID 1667101Notes

Reaction equation

HRID 1667101 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[O:18]=[C:19]1[C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:21][N:20]1[CH2:36][C:37](O)=[O:38].C(N(C(C)C)CC)(C)C>ClCCl>[O:38]=[C:37]([N:10]1[CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:13]=[CH:14][CH:15]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:4]=2)[CH2:8][CH2:9]1)[CH2:36][N:20]1[CH2:21][CH2:22][C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]1=[O:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20608551-(3-(Trifluoromethyl)benzyl)piperazineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45274309HCID 45274309, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(3-(trifluoromethyl)benzyl)piperazine (0.090 g, 0.368 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.140 g, 0.368 mmol) and 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.099 g, 0.335 mmol) in dichloromethane (1.0 mL) was added diisopropylethylamine (0.088 mL, 0.502 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was concentrated and loaded onto silica gel. The product was eluted using a gradient of 5% to 100% ethyl acetate/hexanes giving incomplete purification. A second chromatography over silica gel using a gradient of 0.5% to 5% methanol/dichloromethane gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.41-7.58 (m, 4H), 7.20-7.37 (m, 10H), 4.19 (s, 2H), 3.60 (t, J=4.8 Hz, 2H), 3.52 (t, J=6.5 Hz, 2H), 3.51 (s, 2H), 3.41 (t, J=4.8 Hz, 2H), 2.81 (t, J=6.5 Hz, 2H), 2.40 (t, J=4.9 Hz, 2H), 2.28 (t, J=4.8 Hz, 2H); MS (ESI−) m/z 520 (M−H)−.

Workup

  1. concentrationThe reaction was concentrated
  2. washThe product was eluted
  3. customa gradient of 5% to 100% ethyl acetate/hexanes giving incomplete purification

Sources & evidence

ORD record
ord-2cb3dac4250b4dc8a418ac3898177a64
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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