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

HRID 474349

反応式

HRID 474349 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0d445c8ca0c942b7947d83ea47e731a2
出典データセット
uspto-grants-2014_01
特許番号
US08637526B2

関連ノート

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