1,2-Dichloroethane → N-[(1S,2R)-2-Hydroxycyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

HRID 1750468Notes

Reaction equation

HRID 1750468 reaction equation
C(N(CC)CC)C.N1C2C(=NC=CC=2)N(O)N=1.C(Cl)CCl.Cl.[NH2:23][C@H:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[OH:29].[N:30]1[N:31]([C:35]2[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=2[C:37](O)=[O:38])[N:32]=[CH:33][CH:34]=1>C(Cl)Cl>[OH:29][C@@H:25]1[CH2:26][CH2:27][CH2:28][C@@H:24]1[NH:23][C:37](=[O:38])[C:36]1[CH:40]=[CH:41][CH:42]=[CH:43][C:35]=1[N:31]1[N:32]=[CH:33][CH:34]=[N:30]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 16211105(1R,2S)-2-aminocyclopentan-1-ol hydrochlorideHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acid

Product 1

HCID 118308343N-[(1S,2R)-2-Hydroxycyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (1.52 ml, 10.90 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (0.59 g, 4.36 mmol) and EDC (0.84 g, 4.36 mmol) were added to a solution of (1R,2S)-2-aminocyclopentan-1-ol hydrochloride (CAS number 137254-03-6; 0.50 g, 3.63 mmol) and 2-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1001401-62-2; 0.76 g, 4.00 mmol) in DCM (10 ml). The reaction was stirred at room temperature for 18 hours and then diluted with DCM (50 ml) and washed with a saturated solution of sodium bicarbonate (2×20 ml). The crude product was purified by column chromatography (silica, 0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. washwashed with a saturated solution of sodium bicarbonate (2×20 ml)
  2. customThe crude product was purified by column chromatography (silica, 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-aab72e95aa694697b640b0eb575ea203
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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