Diisopropylethylamine → 2,6-Dimethoxy-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide

HRID 1750573Notes

Reaction equation

HRID 1750573 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.Cl.[NH2:13][C@H:14]1[CH2:18][CH2:17][CH2:16][C@@H:15]1[NH:19][C:20](=[O:31])[C:21]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=1[O:29][CH3:30].CCN(C(C)C)C(C)C>CS(C)=O>[CH3:30][O:29][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:21]=1[C:20]([NH:19][C@H:15]1[CH2:16][CH2:17][CH2:18][C@@H:14]1[NH:13][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1)=[O:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 118308159N-((1S,2S)-2-aminocyclopentyl)-2,6-dimethoxybenzamide hydrochloride2×

Product 1

HCID 1183082042,6-Dimethoxy-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-chloro-5-(trifluoromethyl)pyridine (CAS number 52334-81-3; 266 mg, 1.46 mmol), N-[(1S,2S)-2-aminocyclopentyl]-2,6-dimethoxybenzamide hydrochloride (Intermediate 5; 400 mg, 1.33 mmol), DIPEA (0.70 ml, 3.99 mmol) and DMSO (4.8 ml) was subjected to microwave irradiation at 140° C. for 2 hours. Upon cooling, the resulting mixture was partitioned between ethyl acetate (10 ml) and water (10 ml) and the combined organics were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was further purified by trituration with di-isopropylether to afford the title compound.

Workup

  1. customirradiation at 140° C. for 2 hours
  2. temperatureUpon cooling
  3. customthe resulting mixture was partitioned between ethyl acetate (10 ml) and water (10 ml)
  4. washthe combined organics were washed with brine (10 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was further purified by trituration with di-isopropylether

Sources & evidence

ORD record
ord-274905b16f324b848c67bb4ad91e39b0
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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