Potassium Carbonate → 4-(3-Benzyloxyphenyl)-N-(2,2,2-trifluoroethanesulfonyl)pyrid-3-ylmethylamine

HRID 392402Notes

Reaction equation

HRID 392402 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[CH2:21][NH2:22])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]([F:31])([F:30])[CH2:25][S:26](Cl)(=[O:28])=[O:27].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[CH2:21][NH:22][S:26]([CH2:25][C:24]([F:31])([F:30])[F:23])(=[O:28])=[O:27])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 867595384-(3-Benzyloxyphenyl)pyridin-3-ylmethylamine

Product 1

HCID 867595374-(3-Benzyloxyphenyl)-N-(2,2,2-trifluoroethanesulfonyl)pyrid-3-ylmethylamine

Reagents, catalysts & solvents 1

HCID 21470604DCE PyridineSolvent

Procedure

A solution of N-(4-(3-benzyloxyphenyl)pyridin-3-ylmethylamine (1.0 equiv.) in 2:1 DCE/Pyridine (0.15 M) was cooled to 0° C. and treated with 2,2,2-trifluoroethanesulfonyl chloride (1.8 equiv.). The mixture was allowed to warm to ambient temperature and stir overnight. The reaction was treated with anhydrous potassium carbonate, stirred for 40 min, and filtered. The filtrate was purified via preparative HPLC eluting with 70:30 to 60:40 DCM/ethyl acetate, evaporated, and then triturated with diethyl ether to give the title compound. Anal Calcd for C21H19F3N2O3S: C, 57.79; H, 4.39; N, 6.42. Found: C, 57.60; H, 4.47; N, 6.41. 1H NMR (400 MHz) 3.77 (2H, q, J=9.0 Hz), 4.86 (2H, d), 4.99 (2H, d), 6.82 (2H, m), 6.95 (1H, m), 7.25 (2H, m), 7.34-7.40 (5H, m), 7.67 (1H, td, J=2.0, 8.0 Hz), 8.32 (1H, bs), 8.50 (1H, d, J=4.0 Hz). MS found 437.1 [M+H]+

Workup

  1. stirringstirred for 40 min
  2. filtrationfiltered
  3. customThe filtrate was purified via preparative HPLC
  4. washeluting with 70:30 to 60:40 DCM/ethyl acetate
  5. customevaporated
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-2e5cda9fc058434c880e2d18915f871f
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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