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

HRID 392402ノート

反応式

HRID 392402 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21470604DCE Pyridine溶媒

実験手順

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]+

後処理

  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

出典と根拠

ORDレコード
ord-2e5cda9fc058434c880e2d18915f871f
出典データセット
uspto-grants-2004_10
特許番号
US06800651B2

反応ノート

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