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Phosgene → HCID 86642313, compound

HRID 906033
Notes
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Reaction equation

HRID 906033 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 1

HCID 86642313HCID 86642313, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8f455b7f253e47dfa356c44ca3655eaa
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08012974B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes