Diisopropylethylamine → tert-Butyl N-[(1S,2S)-2-{[3-bromo-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]carbamate

HRID 1750527Notes

Reaction equation

HRID 1750527 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].[Br:15][C:16]1[C:17](Cl)=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.CCN(C(C)C)C(C)C>CS(C)=O>[Br:15][C:16]1[C:17]([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:18][CH:19]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 135360613-Bromo-2-chloro-5-(trifluoromethyl)pyridineHCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamine

Product 1

HCID 118308134tert-Butyl N-[(1S,2S)-2-{[3-bromo-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]carbamate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 2 g, 9.99 mmol), 3-bromo-2-chloro-5-(trifluoromethyl)pyridine (CAS number 71701-92-3; 2.86 g, 10.98 mmol), DIPEA (1.74 ml, 9.99 mmol) in DMSO (35 ml) was heated at 140° C. for 5 hours. The reaction was partitioned between ethyl acetate and water. The phases were separated and the aqueous layer was re-extracted with ethyl acetate (2×50 ml). The combined organics were washed with brine (50 ml), filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-50% ethyl acetate/petrol), then by column chromatography (silica, 0-15% ethyl acetate/petrol) and then by column chromatography (silica, 0-10% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe phases were separated
  3. extractionthe aqueous layer was re-extracted with ethyl acetate (2×50 ml)
  4. washThe combined organics were washed with brine (50 ml)
  5. filtrationfiltered through a hydrophobic frit
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (silica, 0-50% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-2053476c529a4ef3b67637c1e2718541
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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