7-Chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-amine → Methyl 4-(7-chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoate

HRID 1409184노트

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HRID 1409184 반응식
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:6]2[N:5]=[C:4]([NH2:15])[CH:3]=1.[Cl-].[CH3:17][O:18][C:19](=[O:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=[C:6]2[N:5]=[C:4]([NH:15][C:24]([C:23]2[CH:27]=[CH:28][C:20]([C:19]([O:18][CH3:17])=[O:29])=[CH:21][CH:22]=2)=[O:25])[CH:3]=1

참가 물질

5

반응물 2

HCID 442513097-Chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-amineHCID 53442854Terephthalic acid monomethylester chloride

생성물 1

HCID 86652275Methyl 4-(7-chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoate수율 10%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매2회

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온도
0 °C

실험 절차

7-chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-amine (0.5 g, 1.0 equivalent) was suspended in pyridine (0.2 M) in a round bottom flask. At 0° C. was added a solution of terephthalic acid monomethylester chloride (2.0 equivalents) pre-dissolved in pyridine (0.8M), and followed by addition of N,N-dimethylpyridin-4-amine (0.1 equivalent). The mixture was stirred vigorously at 0° C. for 48 h. The reaction was quenched with saturated NaHCO3; pyridine was removed in vacuo and the residue was extracted with EtOAc twice and the combined organic layers were dried over Na2SO4. The organic layers were concentrated in vacuo and the crude mixture was purified using chromatography (SiO2, gradient of 10 to 50% EtOAc/hexanes) to afford the titled compound (10%) as a solid. Melting point (191.0-195.0° C.). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.90 (s, 3H) 7.20 (s, 1H) 8.06-8.11 (m, 2H) 8.12-8.18 (m, 2H) 8.32 (s, 1H) 11.88 (s, 1H); ESI-MS: m/z 399.0 (M+H)+.

후처리

  1. customThe reaction was quenched with saturated NaHCO3
  2. custompyridine was removed in vacuo
  3. extractionthe residue was extracted with EtOAc twice
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationThe organic layers were concentrated in vacuo
  6. customthe crude mixture was purified

출처 및 근거

ORD 기록
ord-64f85fe5104145589995e434430f9124
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921358B2

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