4-Piperidinecarboxylic acid → 1-(5-Boronopyrimidin-2-yl)piperidine-4-carboxylic acid

HRID 626927

반응식

HRID 626927 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=1.[NH:11]1[CH2:19][CH2:18][CH:14]([C:15]([OH:17])=[O:16])[CH2:13][CH2:12]1.C(N(CC)CC)C>C(O)C>[B:8]([C:5]1[CH:4]=[N:3][C:2]([N:11]2[CH2:19][CH2:18][CH:14]([C:15]([OH:17])=[O:16])[CH2:13][CH2:12]2)=[N:7][CH:6]=1)([OH:10])[OH:9]

참가 물질

5

반응물 3

HCID 37734-Piperidinecarboxylic acidHCID 8471TriethylamineHCID 21747362(2-Chloropyrimidin-5-yl)boronic acid

생성물 1

HCID 899237011-(5-Boronopyrimidin-2-yl)piperidine-4-carboxylic acid수율 60.3%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

2-Chloropyrimidin-5-ylboronic acid (2.00 g, 12.6 mmol) and isonipecotic acid (1.63 g, 12.6 mmol) were suspended in ethanol (25 mL). Triethylamine (1.78 mL, 12.6 mmol) was added and the mixture was heated at 80° C. for 16 h. The reaction mixture was cooled and concentrated in vacuo to dryness. Water (30 mL) was added and the reaction mixture was swirled until the product completely dissolved. On standing, crystallisation occurred. The mixture was cooled in an ice bath for 30 minutes, then filtered. The resultant solid was washed sparingly with water and dried under suction, then freeze-dried, to give the title compound (1.90 g, 7.6 mmol, 60%) as a white solid. δH (d6-DMSO) 8.60 (s, 2H), 8.06 (br s, 2H), 4.60-4.52 (m, 2H), 3.14-3.02 (m, 2H), 2.60-2.54 (m, 1H), 1.90-1.80 (m, 2H), 1.55-1.39 (m, 2H). LCMS (ES+) 252 (M+H)+.

후처리

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo to dryness
  3. additionWater (30 mL) was added
  4. dissolutioncompletely dissolved
  5. customcrystallisation
  6. temperatureThe mixture was cooled in an ice bath for 30 minutes
  7. filtrationfiltered
  8. washThe resultant solid was washed sparingly with water
  9. customdried under suction
  10. customfreeze-dried

출처 및 근거

ORD 기록
ord-fb916736a0044af3bdda5eab0620f97b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309243B2

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