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

HRID 2242803노트

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HRID 2242803 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-d011efb0e73d4f40bb6c6989c6fec150
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674788B2

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