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

HRID 1750703Notes

Reaction equation

HRID 1750703 reaction equation
[CH3:1][C@:2]1([NH:8][C:9]2[CH:14]=[N:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][N:10]=2)[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH2:7].[N:19]1[CH:24]=[CH:23][CH:22]=[N:21][C:20]=1[C:25]1[C:26]([C:31](O)=[O:32])=[N:27][CH:28]=[CH:29][CH:30]=1.C(N(CC)CC)C.N1C2C(=NC=CC=2)N(O)N=1.C(Cl)CCl>C(Cl)Cl>[CH3:1][C@:2]1([NH:8][C:9]2[CH:14]=[N:13][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:11][N:10]=2)[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:31]([C:26]1[C:25]([C:20]2[N:19]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:30][CH:29]=[CH:28][N:27]=1)=[O:32]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 593636623-(Pyrimidin-2-yl)pyridine-2-carboxylic acidHCID 118308048(1S,2S)-1-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine2×

Product 1

HCID 118308050N-[(1S,2S)-2-Methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(pyrimidin-2-yl)pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 50 mg, 0.192 mmol), 3-(pyrimidin-2-yl)pyridine-2-carboxylic acid (CAS number 1228431-21-7; 46 mg, 0.231 mmol), triethylamine (80 ul, 0.576 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (34 mg, 0.250 mmol) and EDC (48 mg, 0.250 mmol) in DCM (5 ml) was stirred at room temperature for 18 hours. The reaction was partitioned between DCM (20 ml) and a saturated solution of sodium bicarbonate (10 ml). The aqueous layer was further extracted with DCM (20 ml) and the combined organics were filtered through a hydrophobic frit 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. customThe reaction was partitioned between DCM (20 ml)
  2. extractionThe aqueous layer was further extracted with DCM (20 ml)
  3. filtrationthe combined organics were filtered through a hydrophobic frit
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (silica, 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-fbd1bd4f4bdf485db925b89345b35e7a
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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