Triethylamine → 3-[5-Amino-4-(2-chlorobenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide

HRID 251356

반응식

HRID 251356 반응식
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6](=[CH:9]NC1C=CC=CC=1)[C:7]#[N:8])=[O:5].FC(F)(F)C(O)=O.[CH:28]1([NH:31][C:32](=[O:42])[C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([NH:40][NH2:41])[CH:34]=2)[CH2:30][CH2:29]1.C(N(CC)CC)C>C(O)C>[NH2:8][C:7]1[N:40]([C:35]2[CH:34]=[C:33]([CH:38]=[CH:37][C:36]=2[CH3:39])[C:32]([NH:31][CH:28]2[CH2:30][CH2:29]2)=[O:42])[N:41]=[CH:9][C:6]=1[C:4](=[O:5])[C:3]1[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=1[Cl:1]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 670242032-(2-Chlorobenzoyl)-3-phenylaminoacrylonitrileHCID 67024207N-cyclopropyl-3-hydrazinyl-4-methylbenzamide 2,2,2-trifluoroacetate

생성물 1

HCID 113268833-[5-Amino-4-(2-chlorobenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide수율 39%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2-(2-chlorobenzoyl)-3-phenylaminoacrylonitrile (93 mg, 0.33 mmol, 1.0 eq), N-cyclopropyl-3-hydrazino-4-methylbenzamide trifluoroacetate (104 mg, 0.33 mmol, 1 eq), and triethylamine (31 μL, 0.22 mmol, 1.0 eq) in 20 mL of ethanol was heated to 60° C. for 48h. After cooling, the mixture was concentrated and the residue was dissolved in minimal ethyl acetate. 100 ml diethyl ether was added and the precipitate was filtered and dried to provide desired product (50 mg, 39%). HPLC (4 minute 10-90 gradient) tR 2.51 min; MS m/z 395.1 [M+H]+; 1H NMR (DMSO), δ 8.50 (d, J=3.8 Hz, 1 H), 7.93 (d, J=8.0 Hz, 1 H), 7.84 (s, 1 H), 7.57 (m, 5H) 7.32 (s, 1 H), 7.01 (s, 2 H) 3.37 (m, 2 H), 2.86 (m, 1 H), 2.14 (s, 3 H), 1.09 (t, 2 H), 0.68 (m, 2 H), 0.58 (m, 2 H) ppm

후처리

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. dissolutionthe residue was dissolved in minimal ethyl acetate
  4. addition100 ml diethyl ether was added
  5. filtrationthe precipitate was filtered
  6. customdried

출처 및 근거

ORD 기록
ord-8d956fa2c8e34b88891ada5f4f8cb292
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863314B2

연결된 노트

불러오는 중…