Triethylamine → N-(1-Adamantyl)-5-(2-[4-morpholinyl]ethoxy)-1-(4-isopropylphenyl)pyrazole-4-carboxamide

HRID 617228

反応式

HRID 617228 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([O:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:13]([C:24](O)=[O:25])[CH:12]=[N:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl.[C:56]12([NH2:66])[CH2:65][CH:60]3[CH2:61][CH:62]([CH2:64][CH:58]([CH2:59]3)[CH2:57]1)[CH2:63]2.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:56]12([NH:66][C:24]([C:13]3[CH:12]=[N:11][N:10]([C:7]4[CH:8]=[CH:9][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:5][CH:6]=4)[C:14]=3[O:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[O:25])[CH2:63][CH:62]3[CH2:61][CH:60]([CH2:59][CH:58]([CH2:64]3)[CH2:57]1)[CH2:65]2

参加物

10

反応物 6

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 64150Amantadine HydrochlorideHCID 757711-HydroxybenzotriazoleHCID 179194001-(4-Isopropylphenyl)-5-(2-[4-morpholinyl]ethoxy)pyrazole-4-carboxylic acid

生成物 1

HCID 9826992N-(1-Adamantyl)-5-(2-[4-morpholinyl]ethoxy)-1-(4-isopropylphenyl)pyrazole-4-carboxamide収率 14.4%

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 1-(4-isopropylphenyl)-5-(2-[4-morpholinyl]ethoxy)pyrazole-4-carboxylic acid (43 mg, 0.12 mmol) in dimethylformamide (1 mL) under an argon atmosphere, was added 1-hydroxybenzotriazole (16 mg, 0.12 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (25 mg, 0.13 mmol), triethylamine (60 uL, 0.43 mmol) and 1-adamantanamine hydrochloride (25 mg, 0.13 mmol). The reaction mixture was stirred for 24 h at room temperature, heated to 70° C. for 2 h, and stirred for another 96 h at room temperature. The resulting mixture was treated with aqueous sodium carbonate, extracted with ethyl acetate, washed with water four times and dried over Na2SO4. The extract was concentrated in vacuo. This coupling was repeated on the same scale and the combined residue was purified by chromatography twice over silica gel eluting the first column with 2 to 3% methanol in chloroform, and the second with 30 to 40% ethyl acetate in chloroform to afford the title compound (7% yield, 8.5 mg) as a yellow powder, mp 132-134° C. MS (ES) m/e 493.4 [M+H]+.

後処理

  1. temperatureheated to 70° C. for 2 h
  2. stirringstirred for another 96 h at room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with water four times
  5. dry with materialdried over Na2SO4
  6. concentrationThe extract was concentrated in vacuo
  7. customthe combined residue was purified by chromatography twice over silica gel eluting the first column with 2 to 3% methanol in chloroform

出典と根拠

ORDレコード
ord-ef57082c3f34480bb8176acc12378372
出典データセット
uspto-grants-1999_09
特許番号
US05948777

関連ノート

読み込み中…