1,2-Dichloroethane → HCID 118308177, compound
Reaction equation
Cl.[F:2][C:3]([F:18])([F:17])[C:4]1[N:5]=[CH:6][C:7]([NH:10][C@H:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2[NH2:16])=[N:8][CH:9]=1.[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[C:23]([C:28](O)=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=1.C(Cl)CCl.N1C2C(=NC=CC=2)N(O)N=1.C(N(CC)CC)C>C(Cl)Cl>[F:32][C:20]([F:19])([F:31])[O:21][C:22]1[C:23]([C:28]([NH:16][C@H:12]2[CH2:13][CH2:14][CH2:15][C@@H:11]2[NH:10][C:7]2[CH:6]=[N:5][C:4]([C:3]([F:2])([F:17])[F:18])=[CH:9][N:8]=2)=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14; 70 mg, 0.25 mmol), 3-(trifluoromethoxy)pyridine-2-carboxylic acid (CAS number 1221171-81-8; 86 mg, 0.42 mmol), EDC (71 mg, 0.37 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (51 mg, 0.37 mmol) and triethylamine (0.104 ml, 0.74 mmol) in DCM (1 ml) was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate (25 ml) and water (10 ml). The organics were washed with water (2×10 ml) and brine (10 ml), dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by reverse phase chromatography (C18 silica, 0-100% water (with 0.05% ammonia)/acetonitrile) to afford the title compound.
Workup
- customThe mixture was partitioned between ethyl acetate (25 ml) and water (10 ml)
- washThe organics were washed with water (2×10 ml) and brine (10 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by reverse phase chromatography (C18 silica, 0-100% water (with 0.05% ammonia)/acetonitrile)
Sources & evidence
- ORD record
- ord-73d9d112d9864cf19973f3ccf916e306
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
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