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Phosgene → HCID 86642313, 화합물

HRID 906033
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HRID 906033 반응식
[CH3:1][Si:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[C:14]([NH2:16])[N:15]=[C:10]2[CH:9]=[CH:8]1.CCN(C(C)C)C(C)C.[C:28](Cl)(Cl)=[O:29].[NH2:32][C@H:33]1[CH2:37][CH2:36][C@H:35]([N:38]2[C:46](=[O:47])[C:45]3[C:40](=[CH:41][C:42](Cl)=[C:43](Cl)[CH:44]=3)[C:39]2=[O:50])[CH2:34]1>C1(C)C=CC=CC=1.CN(C=O)C.C(Cl)Cl>[O:50]=[C:39]1[C:40]2[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:46](=[O:47])[N:38]1[C@H:35]1[CH2:36][CH2:37][C@H:33]([NH:32][C:28]([NH:16][C:14]2[N:15]=[C:10]3[CH:9]=[CH:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:18])([CH3:17])[CH3:1])[C:11]3=[N:12][CH:13]=2)=[O:29])[CH2:34]1
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8

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HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 593633695-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamineHCID 86642300trans 2-(3-Amino-cyclopentyl)-5,6-dichloro-isoindole-1,3-dione

생성물 1

HCID 86642313HCID 86642313, 화합물수율 75%

시약·촉매·용매 3

HCID 1140
Toluene
용매
HCID 6228Dimethylformamide용매
HCID 6344Dichloromethane용매

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온도
-20 °C

실험 절차

In an oven dried flask was added 5-(2-trimethylsilanyl-ethoxymethyl)-5H pyrrolo[2,3-b]pyrazin-2-ylamine (0.118 g, 0.45 mmol), DIPEA (0.275 mL, 1.58 mmol) and 5 mL DCM and the flask cooled under N2 in a dry ice acetone bath. A 20% solution of phosgene in toluene was added (0.284 mL, 0.54 mmol) and the purplish red solution was stirred for 20 minutes then warmed to −20° C. A solution of trans 2-(3-amino-cyclopentyl)-5,6-dichloro-isoindole-1,3-dione (0.143 g, est 0.5 mmol, mixture with monochloro derivative) in 8 mL DMF was added and stirred for 60 minutes, quench with MeOH and concentrated in vacuo. The residue was mixed with MeOH, filtered and the solid rinsed with MeOH and dried in vacuo to give trans 1-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclopentyl]-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (0.196 g, 75% yield).

후처리

  1. customIn an oven dried flask
  2. temperaturethe flask cooled under N2 in a dry ice acetone bath
  3. stirringstirred for 60 minutes
  4. customquench with MeOH
  5. concentrationconcentrated in vacuo
  6. additionThe residue was mixed with MeOH
  7. filtrationfiltered
  8. washthe solid rinsed with MeOH
  9. customdried in vacuo

출처 및 근거

ORD 기록
ord-8f455b7f253e47dfa356c44ca3655eaa
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012974B2

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