1,2-Dichloroethane → 3-Bromo-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide

HRID 1750595Notes

Reaction equation

HRID 1750595 reaction equation
C(Cl)CCl.[Br:5][C:6]1[C:7]([C:12]([OH:14])=O)=[N:8][CH:9]=[CH:10][CH:11]=1.N1C2C(=NC=CC=2)N(O)N=1.Cl.[F:26][C:27]([F:42])([F:41])[C:28]1[N:29]=[CH:30][C:31]([NH:34][C@H:35]2[CH2:39][CH2:38][CH2:37][C@@H:36]2[NH2:40])=[N:32][CH:33]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:5][C:6]1[C:7]([C:12]([NH:40][C@H:36]2[CH2:37][CH2:38][CH2:39][C@@H:35]2[NH:34][C:31]2[CH:30]=[N:29][C:28]([C:27]([F:42])([F:41])[F:26])=[CH:33][N:32]=2)=[O:14])=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 20501293-Bromopyridine-2-carboxylic AcidHCID 118308118(1S,2S)-1-N-[5-(Trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×

Product 1

HCID 1183082783-Bromo-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

EDC (509 mg, 2.65 mmol) was added to a solution of 3-bromopyridine-2-carboxylic acid (429 mg, 2.12 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (361 mg, 2.65 mmol), (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14, 500 mg, 1.77 mmol) and triethylamine (0.74 ml, 5.31 mmol) in DCM (5.9 ml). The reaction was stirred at room temperature overnight. The reaction was diluted with DCM, washed with water, brine, filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica 0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. washwashed with water, brine
  2. filtrationfiltered through a hydrophobic frit
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (silica 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-be55bcd175a2422d9d1decd380eb9c2e
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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