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

HRID 659782

반응식

HRID 659782 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-e8361d8943ed48b8b3d4e8688c346a2f
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080666B2

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