Diisopropylethylamine → 5-amino-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-3-methylsulfanyl-1H-pyrazole-4-carboxylic acid amide

HRID 251351

反応式

HRID 251351 の反応式
[C:1]([C:3](=[C:7](SC)[S:8][CH3:9])[C:4]([NH2:6])=[O:5])#[N:2].FC(F)(F)C(O)=O.[CH:19]1([NH:22][C:23](=[O:33])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([NH:31][NH2:32])[CH:25]=2)[CH2:21][CH2:20]1.C(N(C(C)C)CC)(C)C>C(O)C>[NH2:2][C:1]1[N:31]([C:26]2[CH:25]=[C:24]([C:23](=[O:33])[NH:22][CH:19]3[CH2:21][CH2:20]3)[CH:29]=[CH:28][C:27]=2[CH3:30])[N:32]=[C:7]([S:8][CH3:9])[C:3]=1[C:4]([NH2:6])=[O:5]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27477462-Cyano-3,3-bis(methylthio)acrylamideHCID 67024207N-cyclopropyl-3-hydrazinyl-4-methylbenzamide 2,2,2-trifluoroacetate

生成物 1

HCID 113713845-amino-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-3-methylsulfanyl-1H-pyrazole-4-carboxylic acid amide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
65 °C

実験手順

To a solution of 2-cyano-3,3-bis-methylsulfanyl-acrylamide 12 (100 mg, 0.574 mmol) in ethanol (5 ml) was added N-cyclopropyl-3-hydrazino-4-methyl-benzamide trifluoroacetic acid salt (0.183 g, 0.574 mmol) and diisopropylethylamine (0.100 ml, 0.574 mmol). The mixture was heated to 65° C. for 18 h. The mixture was cooled to room temperature. Solvents were removed in vacuo. EtOAc was added to the residue and a solid precipitated. The solid was collected on a fritted funnel and was washed with EtOAc and ether to give the desired 5-amino-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-3-methylsulfanyl-1H-pyrazole-4-carboxylic acid amide 13. HPLC (4 minute 10-90 gradient) tR 1.98 min; MS m/z 439.08 [M+H]+; 1H NMR (DMSO-d6, 500 MHz) δ 8.47 (d, J=3.7, 1 H), 7.90 (d, J=7.9, 1 H), 7.78 (s, 1 H), 7.49 (d, J=8.0, 1 H), 6.81 (bs, 2 H), 6.30 (s, 2 H), 2.86 (m, 1 H), 2.45 (s, 3 H), 2.11 (s, 3 H), 0.68 (m, 2 H), 0.57 (m, 2 H) ppm.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customSolvents were removed in vacuo
  3. additionEtOAc was added to the residue
  4. customa solid precipitated
  5. customThe solid was collected on a fritted funnel
  6. washwas washed with EtOAc and ether

出典と根拠

ORDレコード
ord-bf8373ef89354b5e85c2f150d48d9843
出典データセット
uspto-grants-2011_01
特許番号
US07863314B2

関連ノート

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