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Diisopropylethylamine → HCID 86592794, 화합물

HRID 1245123
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HRID 1245123 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[C:11]([C:17](O)=[O:18])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.Cl.[CH3:21][O:22][C:23](=[O:43])[C@@H:24]([NH2:42])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:21][O:22][C:23](=[O:43])[CH:24]([NH:42][C:17]([C:11]1[CH:10]=[N:9][N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:12]=1[C:13]([F:16])([F:14])[F:15])=[O:18])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:40])([F:39])[F:41])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 50570101-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidHCID 46172856HCID 46172856, 화합물

생성물 1

HCID 86592794HCID 86592794, 화합물수율 47.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1-(4-Fluoro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (0.300 g, 1.097 mmol, prepared in example 635) in DMF (4.0 mL) was reacted with (2S)-amino-3-(4′-trifluoromethyl-biphenyl-4-yl)propionic acid methyl ester Hydrochloride (0.394 g, 1.097 mmol), HBTU (0.416 g, 1.097 mmol), and DIEA (0.585 mL, 3.29 mmol) as described in general procedure A. The crude compound was purified by washing with ethyl ether to give 0.300 g (47%) of 2-{[1-(4-Fluoro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carbonyl]-amino}-3-(4′-trifluoromethyl-biphenyl-4-yl)-propionic acid methyl ester. A solution of this ester (0.125 g, 0.215 mmol) in THF (4.0 mL) was treated with LiOH (0.031 g) by general procedure I to afford (0.105 g, 87%) the title compound 2-{[1-(4-Fluoro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carbonyl]-amino}-3-(4′-trifluoromethyl-biphenyl-4-yl)-propionic acid as a white solid. LCMS: 565 (M+1)+. 1H NMR (DMSO-d6) 8.92 [d, 1H], 8.39 [s, 1H], 8.18 [d, 2H], 8.09 [d, 2H], 7.96 [d, 2H], 7.87 [m, 2H], 7.71 [m, 4H], 4.83 [m, 1H], 3.58 [m, 1H], 3.36 [m, 1H].

후처리

  1. customThe crude compound was purified
  2. washby washing with ethyl ether

출처 및 근거

ORD 기록
ord-f83b95a2baaa456e93778b298ce72966
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07122580B2

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