3,4-dihydro-2H-pyran → tetrahydro-pyran-2-yl-1H-pyrazole-3-carboxylic acid [4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-amide

HRID 659782

反応式

HRID 659782 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[C:15]([N+]([O-])=O)=[CH:14][NH:13][N:12]=2)=[O:10])[CH2:4][CH2:3]1.[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH2:38]1>C(Cl)Cl.C(Cl)(Cl)Cl.C1COCC1>[O:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]1[O:1][CH:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][N:13]([CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42][O:37]3)[N:12]=2)=[O:10])[CH2:6][CH2:7]1

参加物

8

反応物 4

HCID 80803,4-dihydro-2H-pyranHCID 186148PyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 178522231HCID 178522231、化合物

生成物 1

HCID 131726921tetrahydro-pyran-2-yl-1H-pyrazole-3-carboxylic acid [4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-amide

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-nitro-1H-pyrazole-3-carboxylic acid 4-hydroxy-cyclohexylamide (1.95 g; 7.67 mmol) in a mix of THF (50 ml) and chloroform (100 ml), was treated with 3,4-dihydro-2H-pyran (1.54 ml, 15.34 mmol) and p-toluenesulphonic acid monohydrate (100 mg). The reaction mixture was stirred at room temperature overnight, and then excess pyran (0.9 ml) was added in total to bring reaction to completion. The reaction mixture was diluted with CH2Cl2 and washed successively with saturated aqueous sodium bicarbonate, water and brine. The resulting solution was reduced in vacuo and subject to Biotage column chromatography, eluting with hexane (2 column lengths) followed by 30% ethyl acetate:hexane (10 column lengths), 70% ethyl acetate:hexane (10 column lengths) to give 1.25 g of 4-nitro-1-(tetrahydro-pyran-2-yl-1H-pyrazole-3-carboxylic acid [4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-amide. (LC/MS: Rt 2.97, [M+H]+ 423).

後処理

  1. customreaction to completion
  2. washwashed successively with saturated aqueous sodium bicarbonate, water and brine
  3. washeluting with hexane (2 column lengths)

出典と根拠

ORDレコード
ord-e8361d8943ed48b8b3d4e8688c346a2f
出典データセット
uspto-grants-2011_12
特許番号
US08080666B2

関連ノート

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