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

HRID 1959513

반응식

HRID 1959513 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 48 h. 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, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.84 (s, 1H), 7.57 (m, 5H) 7.32 (s, 1H), 7.01 (s, 2H) 3.37 (m, 2H), 2.86 (m, 1H), 2.14 (s, 3H), 1.09 (t, 2H), 0.68 (m, 2H), 0.58 (m, 2H) 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-07c9c9751de643439fef6e3dd3a5ed92
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410160B2

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