Nitric Acid → 5-[(2R)-2-(2,5-Difluorophenyl)-1-pyrrolidinyl]-3-nitropyrazolo[1,5-a]pyrimidine

HRID 1893761노트

반응식

HRID 1893761 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][CH:22]=[C:16]2[N:15]=1.[N+:23]([O-])([OH:25])=[O:24]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:16]2[N:15]=1

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 67329909(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine

생성물 1

HCID 673298195-[(2R)-2-(2,5-Difluorophenyl)-1-pyrrolidinyl]-3-nitropyrazolo[1,5-a]pyrimidine수율 58%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine (3.3 g, 10.99 mmol), was dissolved in 25 mL TFA at ambient temperature to give a clear yellowish solution, then nitric acid (3.434 mL, 54.94 mmol) was added drop-wise to the solution with rapid stirring. After addition, the reaction mixture was stirred for another 15 minutes at ambient temperature, then quenched by pouring onto ice with rapid stirring. The resulting yellowish suspension was filtered, rinsed with water, then the solid was triturated with MeOH (50 mL, with brief sonication), and vacuum-filtered, giving the pure product as a fine off-white powder (2.2 g, 58% yield).

후처리

  1. customto give a clear yellowish solution
  2. additionAfter addition
  3. customquenched
  4. additionby pouring onto ice with rapid stirring
  5. filtrationThe resulting yellowish suspension was filtered
  6. washrinsed with water
  7. customthe solid was triturated with MeOH (50 mL, with brief sonication)
  8. filtrationvacuum-filtered

출처 및 근거

ORD 기록
ord-9310ba69f4604ceeac65b8ea559ba0f8
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513263B2

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