Diisopropylethylamine → HCID 118308243, compound

HRID 1750565Notes

Reaction equation

HRID 1750565 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[NH2:12][C@H:13]1[CH2:17][CH2:16][CH2:15][C@@H:14]1[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].CCN(C(C)C)C(C)C>CS(C)=O>[F:9][C:8]([F:11])([F:10])[C:5]1[N:6]=[CH:7][C:2]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[N:3][CH:4]=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 2-chloro-5-(trifluoromethyl)pyrazine (CAS number 799557-87-2; 6.78 ml, 54.9 mmol), tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 10 g, 49.9 mmol) and DIPEA (26.2 ml, 150 mmol) in DMSO (160 ml) was heated at 140° C. for 18 hours. The reaction mixture was partitioned between ethyl acetate (200 ml) and water (200 ml). The aqueous layer was extracted with ethyl acetate (2×100 ml). The combined organics were washed with brine (3×100 ml), filtered through a hydrophobic frit, further dried over magnesium sulphate and then concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-40% ethyl acetate/petrol). Impure fractions were further purified by column chromatography (silica, 10-40% ethyl acetate/petrol) and combined to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (200 ml) and water (200 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×100 ml)
  3. washThe combined organics were washed with brine (3×100 ml)
  4. filtrationfiltered through a hydrophobic frit
  5. dry with materialfurther dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (silica, 0-40% ethyl acetate/petrol)
  8. customImpure fractions were further purified by column chromatography (silica, 10-40% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-7e958b3e1f564557a60831b76e00a59d
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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