1,2-Dichloroethane → HCID 118308056, compound

HRID 1750668Notes

Reaction equation

HRID 1750668 reaction equation
Cl.[F:2][C:3]([F:18])([F:17])[C:4]1[CH: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]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]2[N:33]=[CH:32][CH:31]=[N:30]2)[C:21]=1[C:22](O)=[O:23].CCN(C(C)C)C(C)C.N1C2C(=NC=CC=2)N(O)N=1.C(Cl)CCl>C(Cl)Cl>[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]2[N:33]=[CH:32][CH:31]=[N:30]2)[C:21]=1[C:22]([NH:16][C@H:12]1[CH2:13][CH2:14][CH2:15][C@@H:11]1[NH:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([F:2])([F:17])[F:18])=[CH:9][N:8]=1)=[O:23]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 670866272-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acidHCID 118308256(1S,2S)-1-N-[5-(Trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride2×

Product 1

HCID 118308056HCID 118308056, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,2S)-1-N-[5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 1; 1.09 g, 3.87 mmol) in DCM (13 ml) was added 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1186050-58-7; 0.802 g, 3.87 mmol), DIPEA (2.027 ml, 11.61 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (0.579 g, 4.26 mmol) and EDC (0.816 g, 4.26 mmol). The reaction was stirred at room temperature for 17 hours and was then partitioned between DCM and a saturated solution of sodium bicarbonate, filtered through a hydrophobic fit and concentrated in vacuo. The residue was purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol) and recrystallised from IPA to afford the title compound.

Workup

  1. customwas then partitioned between DCM
  2. filtrationa saturated solution of sodium bicarbonate, filtered through a hydrophobic fit
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol)
  5. customrecrystallised from IPA

Sources & evidence

ORD record
ord-216ed517eda8469ab092a9cd1a958954
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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