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Phosgene → HCID 86642313、化合物

HRID 906033
ノート
印刷プレビュー

反応式

HRID 906033 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

HCID 86642313HCID 86642313、化合物収率 75%

試薬・触媒・溶媒 3

HCID 1140
Toluene
溶媒
HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8f455b7f253e47dfa356c44ca3655eaa
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08012974B2

反応ノート

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