4-Methylmorpholine → HCID 67358405, compound

HRID 1667276Notes

Reaction equation

HRID 1667276 reaction equation
[O:1]=[C:2]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20](Cl)=[O:21].[F:23][C:24]([F:33])([F:32])[C:25]1[CH:26]=[CH:27][C:28]([NH2:31])=[N:29][CH:30]=1.CN1CCOCC1>ClCCl>[O:1]=[C:2]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([NH:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([F:32])([F:23])[F:33])=[CH:30][N:29]=1)=[O:21]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 86640843HCID 86640843, compound

Product 1

HCID 67358405HCID 67358405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetyl chloride (Example 246A, 0.157 g, 0.5 mmol) dissolved in dichloromethane (5 mL) was added 5-(trifluoromethyl)pyridin-2-amine (0.081 g, 0.5 mmol) and N-methylmorpholine (0.085 mL, 0.75 mmol) under nitrogen. After stirring for 18 hours, the reaction mixture was concentrated, loaded onto silica gel column (Analogix®, Burlington, Wis.) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes (Flow=30 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 8.70 (s, 1H), 8.53 (s, 1H), 8.24 (d, J=8.7, 1H), 7.90 (dd, J=2.3, 8.8, 1H), 7.44-7.18 (m, 10H), 4.21 (s, 2H), 3.55 (t, J=6.5, 2H), 2.88 (t, J=6.5, 2H); MS (DCI) m/z 440.1 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. washthe product eluted with a gradient of 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes (Flow=30 mL/minute) over 30 minutes

Sources & evidence

ORD record
ord-796690aaa01440cca72a47bf82294ff4
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…