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Isopropyl chloroformate → 4-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid isopropyl ester

HRID 557765
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HRID 557765 반응식
Cl.[N:2]1([C:8]2[N:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[N:18]=[C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:20][C:21]=3[C:22]([F:25])([F:24])[F:23])=[O:16])=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH:39]([O:42][C:43](Cl)=[O:44])([CH3:41])[CH3:40]>C(Cl)Cl>[CH:39]([O:42][C:43]([N:5]1[CH2:6][CH2:7][N:2]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]([C:17]3[N:18]=[C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:20][C:21]=3[C:22]([F:24])([F:25])[F:23])=[O:16])=[CH:12][N:13]=2)[CH2:3][CH2:4]1)=[O:44])([CH3:41])[CH3:40]
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참가 물질

5

반응물 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 667381792-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide hydrochloride salt

생성물 1

HCID 576520844-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid isopropyl ester

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

To a suspension of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide hydrochloride salt (50 mg, 0.102 mmol) in methylene chloride (6 mL) was added triethylamine (0.1 mL). The clear solution was cooled in an ice bath and isopropylchloroformate (1M in toluene, 0.2 mL) was added. The mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hr. The solvents were evaporated and the residue was triturated with methanol. The precipitate was filtered and dried to give 4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid isopropyl ester (32.4 mg). LC-MS calcd for C24H24F3N5O4 (m/e) 503.2, obsd 503.8 (M+H). The NMR spectrum obtained on the sample is compatible with its structure.

후처리

  1. temperatureThe clear solution was cooled in an ice bath
  2. customThe solvents were evaporated
  3. customthe residue was triturated with methanol
  4. filtrationThe precipitate was filtered
  5. customdried

출처 및 근거

ORD 기록
ord-28b9e6de1e034f59ad8c4b032477492c
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08058299B2

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