Piperazine → 6-chloro-7-((R)-3-hydroxypyrrolidin-1-yl)-2-piperazin-1-yl-4-pyrrolidin-1-yl-pteridine

HRID 330852노트

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HRID 330852 반응식
[N:1]1([C:6]2[C:15]3[C:10](=[N:11][C:12](Cl)=[C:13]([Cl:16])[N:14]=3)[N:9]=[C:8](Cl)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:19][C@@H:20]1[CH2:24][CH2:23][NH:22][CH2:21]1.C(N(C(C)C)CC)(C)C.[NH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>O1CCOCC1>[Cl:16][C:13]1[N:14]=[C:15]2[C:10](=[N:11][C:12]=1[N:22]1[CH2:23][CH2:24][C@@H:20]([OH:19])[CH2:21]1)[N:9]=[C:8]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[N:7]=[C:6]2[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 4837PiperazineHCID 81531DiisopropylethylamineHCID 2759337(R)-3-PyrrolidinolHCID 137998844-Pyrrolidin-1-yl-2,6,7-trichloropteridine

생성물 1

HCID 866167646-chloro-7-((R)-3-hydroxypyrrolidin-1-yl)-2-piperazin-1-yl-4-pyrrolidin-1-yl-pteridine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

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온도
40 °C

실험 절차

a)+b) 80 mg (0.26 mmol) 4-pyrrolidin-1-yl-2,6,7-trichloro-pteridine are dissolved in 5 ml dioxane and combined with 72 mg (0.58 mmol) (R)-3-hydroxypyrrolidin and 100 μl (0.75 mmol) diisopropylethylamine The mixture is stirred for approx. 30 h at 40° C. The reaction mixture is then slowly added dropwise to a solution of 113 mg (1 mmol) piperazine in 15 ml dioxane at a temperature of 80° C. The mixture is stirred for approx. 16 h at 80° C., cooled to ambient temperature and then poured onto ice water. It is extracted with dichloromethane, the organic phase is dried on sodium sulphate and the solvent is eliminated in vacuo. The residue is purified by chromatography. Yield 68.8 mg (65% of theoretical).

후처리

  1. stirringThe mixture is stirred for approx. 16 h at 80° C.
  2. temperaturecooled to ambient temperature
  3. additionpoured onto ice water
  4. extractionIt is extracted with dichloromethane
  5. customthe organic phase is dried on sodium sulphate
  6. customThe residue is purified by chromatography

출처 및 근거

ORD 기록
ord-f20bfdef58e546ee9ef03a6e31a1feaa
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877756B2

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