1,2-Dichloroethane → N-[(1S,2S)-4,4-Difluoro-2-(2-methylpropane-2-sulfonamido)cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

HRID 1750562Notes

Reaction equation

HRID 1750562 reaction equation
[NH2:1][C@H:2]1[CH2:6][C:5]([F:8])([F:7])[CH2:4][C@@H:3]1[NH:9][S:10]([C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:12])=[O:11].[N:17]1[N:18]([C:22]2[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=2[C:24](O)=[O:25])[N:19]=[CH:20][CH:21]=1.C(Cl)CCl.N1C2C(=NC=CC=2)N(O)N=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:8][C:5]1([F:7])[CH2:6][C@H:2]([NH:1][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[N:18]2[N:19]=[CH:20][CH:21]=[N:17]2)[C@@H:3]([NH:9][S:10]([C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:12])=[O:11])[CH2:4]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acidHCID 118308227N-[(1S,2S)-2-Amino-4,4-difluorocyclopentyl]-2-methylpropane-2-sulfonamide

Product 1

HCID 118308263N-[(1S,2S)-4,4-Difluoro-2-(2-methylpropane-2-sulfonamido)cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(1S,2S)-2-amino-4,4-difluorocyclopentyl]-2-methylpropane-2-sulfonamide (1.03 g, 4.02 mmol) in dry DCM (13.4 ml) was added 2-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1001401-62-2; 0.91 g, 4.82 mmol), EDC (2.31 g, 12.06 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (1.64 g, 12.06 mmol) and DIPEA (2.11 ml, 12.06 mmol). The reaction was stirred at room temperature overnight then partitioned between ethyl acetate and water. The organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography (silica, 30-80% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customthen partitioned between ethyl acetate and water
  2. washThe organics were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by column chromatography (silica, 30-80% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-2d4728b1d7af4d79bbbf15a494f4a561
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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