Diisopropylethylamine → HCID 118308181, compound

HRID 1750635Notes

Reaction equation

HRID 1750635 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[N:8]([CH:21]1[CH2:24][CH2:23][CH2:22]1)[C:9](=[O:20])[C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[O:18][CH3:19].Cl[C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=1.CCN(C(C)C)C(C)C>CS(C)=O>[CH:21]1([N:8]([C@H:4]2[CH2:5][CH2:6][CH2:7][C@@H:3]2[NH:2][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=2)[C:9](=[O:20])[C:10]2[C:11]([O:18][CH3:19])=[CH:12][CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 118308235HCID 118308235, compound2×

Product 1

HCID 118308181HCID 118308181, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-[(1S,2S)-2-aminocyclopentyl]-N-cyclobutyl-2,6-dimethoxybenzamide hydrochloride (Intermediate 18; 200 mg, 0.56 mmol) in dry DMSO (1.9 ml) was added 2-chloro-5-(trifluoromethyl)pyridine (CAS number 52334-81-3; 153 mg, 0.85 mmol) and DIPEA (295 μl, 1.69 mmol). The reaction subjected to microwave irradiation at 150° C. for 2 hours and then was partitioned between ethyl acetate and water. The organics were washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. This was then purified using column chromatography (silica, 0-100% ethyl acetate/petrol) and then further purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.

Workup

  1. customirradiation at 150° C. for 2 hours
  2. customwas partitioned between ethyl acetate and water
  3. washThe organics were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThis was then purified
  7. customfurther purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia)

Sources & evidence

ORD record
ord-98e44841b99b4060808c30a9e863d897
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…