Sodium Hydroxide → 5-(6-Trifluoromethyl-pyridin-2-ylamino)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 474349

반응식

HRID 474349 반응식
[F:1][C:2]([F:25])([F:24])[C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][N:13]3[N:16]=[CH:17][C:18]([C:19]([O:21]CC)=[O:20])=[C:12]3[N:11]=2)[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[F:24][C:2]([F:1])([F:25])[C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][N:13]3[N:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[C:12]3[N:11]=2)[CH:6]=[CH:5][CH:4]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 58063370Ethyl 5-(6-(trifluoromethyl)pyridin-2-ylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylate

생성물 1

HCID 580631475-(6-Trifluoromethyl-pyridin-2-ylamino)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid수율 112.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of ethyl 5-(6-(trifluoromethyl)pyridin-2-ylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylate (344 mg, 0.98 mmol, 1.0 equiv), 2M aqueous sodium hydroxide solution (1.50 mL, 3.0 equiv) and ethanol (15 mL) was heated to reflux for 5 hours. After cooling, the precipitate was collected by filtration, washed with ethanol, and air dried. The resultant solid was suspended in 1.25 M HCl in methanol (16 mL) and then concentrated under vacuum. The residue was triturated (diethyl ether) to afford 355 mg (quant. yield) of 5-(6-trifluoromethyl-pyridin-2-ylamino)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid which was used without further purification. LCMS (ESI) m+H=324.2; 1H NMR (300 MHz, DMSO-d6) δ: 11.03 (s, 1H), 9.01 (d, 1H), 8.95 (d, 1H), 8.35 (s, 1H), 8.10-8.02 (m, 1H), 7.54 (d, 1H), 7.16 (d, 1H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with ethanol, and air
  6. customdried
  7. concentrationconcentrated under vacuum
  8. customThe residue was triturated (diethyl ether)

출처 및 근거

ORD 기록
ord-0d445c8ca0c942b7947d83ea47e731a2
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637526B2

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