Diisopropylethylamine → HCID 118308243, compound

HRID 1750518Notes

Reaction equation

HRID 1750518 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].Cl[C:16]1[CH:21]=[N:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=1.CCN(C(C)C)C(C)C>CS(C)=O>[F:23][C:22]([F:25])([F:24])[C:19]1[N:20]=[CH:21][C:16]([NH:1][C@H:2]2[CH2:6][CH2:5][CH2:4][C@@H:3]2[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamineHCID 189876452-Chloro-5-(trifluoromethyl)pyrazine

Product 1

HCID 118308243HCID 118308243, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 1 g, 4.99 mmol), 2-chloro-5-(trifluoromethyl)pyrazine (CAS number 799557-87-2; 1.09 g, 5.99 mmol) and DIPEA (2.62 ml, 14.98 mmol) in DMSO (17 ml) was subjected to microwave irradiation at 140° C. for 1 hour. The reaction was partitioned between ethyl acetate and water, washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customirradiation at 140° C. for 1 hour
  2. customThe reaction was partitioned between ethyl acetate and water
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (silica, 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-099b5ba8436b42818a6516957a55482e
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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