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

HRID 1750717Notes

Reaction equation

HRID 1750717 reaction equation
Cl.C[N:3]([C:10]1[CH:15]=[N:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1)[C@H:4]1[CH2:8][CH2:7][CH2:6][C@@H:5]1[NH2:9].[N:20]1[CH:25]=[CH:24][CH:23]=[N:22][C:21]=1[C:26]1[C:27]([C:32]([OH:34])=O)=[N:28][CH:29]=[CH:30][CH:31]=1.N1C2[C:38](=NC=CC=2)N(O)N=1.C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl>[CH3:38][C:15]1[C:10]([NH:3][C@H:4]2[CH2:8][CH2:7][CH2:6][C@@H:5]2[NH:9][C:32]([C:27]2[C:26]([C:21]3[N:22]=[CH:23][CH:24]=[CH:25][N:20]=3)=[CH:31][CH:30]=[CH:29][N:28]=2)=[O:34])=[N:11][CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[N:14]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 593636623-(Pyrimidin-2-yl)pyridine-2-carboxylic acidHCID 118308127(1S,2S)-1-N-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×

Product 1

HCID 118308253N-[(1S,2S)-2-{[3-Methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(pyrimidin-2-yl)pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,2S)-1-N-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 23; 100 mg, 0.34 mmol) in DCM (1.2 ml) was added 3-(pyrimidin-2-yl)pyridine-2-carboxylic acid (CAS number 1228431-21-7; 81 mg, 0.40 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (69 mg, 0.51 mmol), EDC (97 mg, 0.51 mmol) and triethylamine (0.14 ml, 1.01 mmol). The reaction was stirred at room temperature for 18 hours and then partitioned between water and DCM, passing through a hydrophobic frit. The organics were concentrated in vacuo and then purified by column chromatography (0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. custompartitioned between water and DCM
  2. concentrationThe organics were concentrated in vacuo
  3. custompurified by column chromatography (0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-5da621a7cacd4962af397c1ec008d192
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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