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

HRID 1750711Notes

Reaction equation

HRID 1750711 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[C:8]([C:13]([OH:15])=O)=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:16][C:17]1([NH:23][C:24]2[N:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)[CH2:21][CH2:20][CH2:19][CH:18]1[NH2:22].N1C2C(=NC=CC=2)N(O)N=1.C(Cl)CCl.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:16][C:17]1([NH:23][C:24]2[N:25]=[CH:26][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:28][N:29]=2)[CH2:21][CH2:20][CH2:19][CH:18]1[NH:22][C:13]([C:8]1[C:7]([C:2]2[N:1]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:15]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 593636623-(Pyrimidin-2-yl)pyridine-2-carboxylic acidHCID 1183081801-Methyl-1-N-[5-(trifluoromethyl)pyrimidin-2-yl]cyclopentane-1,2-diamine2×

Product 1

HCID 118308088N-(2-Methyl-2-{[5-(trifluoromethyl)pyrimidin-2-yl]amino}cyclopentyl)-3-(pyrimidin-2-yl)pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(pyrimidin-2-yl)pyridine-2-carboxylic acid (CAS number 1228431-21-7; 80 mg, 0.40 mmol), 1-methyl-1-N-[5-(trifluoromethyl)pyrimidin-2-yl]cyclopentane-1,2-diamine (Intermediate 50; 103 mg, 0.40 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (81 mg, 0.60 mmol), EDC (114 mg, 0.60 mmol) and DIPEA (0.208 ml, 1.19 mmol) in DCM (4 ml) was stirred at room temperature for 4 days. The reaction was diluted with DCM (5 ml) and a saturated solution of sodium bicarbonate (5 ml), filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by reverse phase chromatography (C18 silica, 5-95% water (0.05% ammonia)/acetonitrile) to afford the title compound.

Workup

  1. filtrationa saturated solution of sodium bicarbonate (5 ml), filtered through a hydrophobic frit
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by reverse phase chromatography (C18 silica, 5-95% water (0.05% ammonia)/acetonitrile)

Sources & evidence

ORD record
ord-caeff7efa6034dd28f5bc2b14ddb31f2
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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