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

HRID 251351

반응식

HRID 251351 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bf8373ef89354b5e85c2f150d48d9843
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863314B2

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