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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Triethylamine → 1-(2,5-Dichloropyrimidin-4-yl)-azetidine-3-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]-amide

HRID 1295671
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HRID 1295671 반응식
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]2)[C:5]([Cl:15])=[CH:4][N:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:37]1[CH:42]=[C:41]([Cl:43])[CH:40]=[C:39]([C@H:44]([NH2:47])[CH2:45][OH:46])[CH:38]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Cl:43][C:41]1[CH:40]=[C:39]([CH:44]([NH:47][C:12]([CH:10]2[CH2:9][N:8]([C:6]3[C:5]([Cl:15])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH2:11]2)=[O:14])[CH2:45][OH:46])[CH:38]=[CH:37][CH:42]=1
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참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59694427(S)-2-amino-2-(3-chlorophenyl)ethanolHCID 878230181-(2,5-Dichloropyrimidin-4-yl)-azetidine-3-carboxylic acid

생성물 1

HCID 90894357
1-(2,5-Dichloropyrimidin-4-yl)-azetidine-3-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]-amide
수율 41%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

1-(2,5-Dichloropyrimidin-4-yl)-azetidine-3-carboxylic acid (66 mg, 0.27 mmol, 1 equivalent) was dissolved in DMF (1 mL) together with EDCI (103 mg, 0.53 mmol, 2 equivalents), HOBt (18 mg, 0.13 mmol, 0.5 equivalent) and (S)-(+)-3-chlorophenylglycinol (67.4 mg, 0.32 mmol, 1.2 equivalents). Triethylamine (121 mg, 0.32 mmol, 1.2 equivalents) was then added and the resulting mixture was stirred at room temperature for 1 hour then warmed to 90° C. for 10 minutes. The crude reaction mixture was diluted with ethyl acetate, washed with water, and the organic fraction dried over sodium sulfate. The resulting crude oil was purified by HPLC Gilson (acetonitrile/water/0.1% TFA), yielding the title compound as a white solid (44 mg, 41%). HPLC Rt=5.528 minutes.

후처리

  1. temperaturethen warmed to 90° C. for 10 minutes
  2. customThe crude reaction mixture
  3. washwashed with water
  4. dry with materialthe organic fraction dried over sodium sulfate
  5. customThe resulting crude oil was purified by HPLC Gilson (acetonitrile/water/0.1% TFA)

출처 및 근거

ORD 기록
ord-32d67224295841c69a7cb4105f0101f4
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07244735B2

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