Triethylamine → 4-(3-Ethoxythiophene-2-carboxamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

HRID 1421481ノート

反応式

HRID 1421481 の反応式
[CH2:1]([O:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9](Cl)=[O:10])[CH3:2].C(OC1C=CSC=1C(O)=O)C.C(Cl)(=O)C(Cl)=O.[NH2:29][C:30]1[C:31]([CH2:39][CH2:40][CH3:41])=[N:32][N:33]([CH3:38])[C:34]=1[C:35]([NH2:37])=[O:36].CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]([NH:29][C:30]1[C:31]([CH2:39][CH2:40][CH3:41])=[N:32][N:33]([CH3:38])[C:34]=1[C:35]([NH2:37])=[O:36])=[O:10])[CH3:2]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27776523-Ethoxythiophene-2-carboxylic acidHCID 33380444-Amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamideHCID 151243963-Ethoxythiophene-2-carbonyl chloride

生成物 1

HCID 53256814-(3-Ethoxythiophene-2-carboxamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

3-Ethoxythiophene-2-carbonyl chloride 2, prepared from the reaction of 3-ethoxythiophene-2-carboxylic acid (2.79 g, 16.2 mmol) with oxalyl chloride, was added to a solution of 4-amino-1-methyl-3-n-propylpyrazole-5-carboxamide 1 (2.08 g, 11.4 mmol), DMAP (28 mg, 0.23 mmol) and Et3N (1.64 g, 16.2 mmol) in anhydrous CH2Cl2 (30 mL) at 0° C., and stirred at r.t. for 24 h. The mixture was washed with 1 N HCl and dried with MgSO4. Chromatography (silica gel, hexane:ethyl acetate=3:1) gave a white solid; mp: 103-104° C.; 1H NMR (DMSO-d6) δ 0.87 (t, J=7 Hz, 3 H), 1.39 (t, J=7 Hz, 3 H), 1.56 (sxt, J=7 Hz, 2 H), 2.43 (t, J=7 Hz, 2 H), 3.88 (s, 3 H), 4.32 (q, J=7 Hz, 2 H), 7.18 (d, J=6 Hz, 1 H), 7.66 (s, br. 1 H), 7.75 (s, br. 1 H), 7.81 (d, J=6 Hz, 1 H), 8.87 (s, 1 H); MS (m/z): 337 (MH+).

後処理

  1. washThe mixture was washed with 1 N HCl
  2. dry with materialdried with MgSO4
  3. customChromatography (silica gel, hexane:ethyl acetate=3:1) gave a white solid

出典と根拠

ORDレコード
ord-19f631e01e5143d2a71c15ae2618bd8a
出典データセット
uspto-grants-2000_06
特許番号
US06077841

反応ノート

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