1,2-Dichloroethane → 2-(5-Methyl-1,3,4-oxadiazol-2-yl)-N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

HRID 1750718Notes

Reaction equation

HRID 1750718 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=O)=[N:4][N:3]=1.[CH3:16][C@:17]1([NH:23][C:24]2[CH:29]=[N:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)[CH2:21][CH2:20][CH2:19][C@@H:18]1[NH2:22].N1C2C(=NC=CC=2)N(O)N=1.C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([NH:22][C@H:18]2[CH2:19][CH2:20][CH2:21][C@:17]2([CH3:16])[NH:23][C:24]2[CH:29]=[N:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)=[O:11])=[N:4][N:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 337001972-(5-Methyl-1,3,4-oxadiazol-2-yl)benzoic acidHCID 118308048(1S,2S)-1-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine2×

Product 1

HCID 1183082442-(5-Methyl-1,3,4-oxadiazol-2-yl)-N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(5-methyl-1,3,4-oxadiazol-2-yl)benzoic acid (CAS number 898289-64-0; 82 mg, 0.40 mmol), (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 80 mg, 0.31 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (54 mg, 0.40 mmol), EDC (77 mg, 0.40 mmol) and triethylamine (0.13 ml, 0.92 mmol) in DCM (3 ml) was stirred at room temperature for 72 hours. The reaction was diluted with DCM and washed with a saturated solution of sodium bicarbonate, passing through a hydrophobic frit and concentrated in vacuo. The crude product was purified by reverse phase chromatography (C18 silica, 5-100% acetonitrile/water with 0.05% ammonia) to afford the title compound.

Workup

  1. washwashed with a saturated solution of sodium bicarbonate
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by reverse phase chromatography (C18 silica, 5-100% acetonitrile/water with 0.05% ammonia)

Sources & evidence

ORD record
ord-c8fea8779f2940bca95acb0054097b98
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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