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Benzylamine → HCID 68543909, compound

HRID 2243486
Notes
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Reaction equation

HRID 2243486 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:19][C:8]2[C:9]3[CH:10]=[CH:11][C:12]([C:16]([OH:18])=O)=[CH:13][C:14]=3[S:15][C:7]=2[C:6]=1[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:19][C:8]2[C:9]3[CH:10]=[CH:11][C:12]([C:16](=[O:18])[NH:46][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:13][C:14]=3[S:15][C:7]=2[C:6]=1[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 68540407HCID 68540407, compound

Product 1

HCID 68543909HCID 68543909, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2,6-dicarboxylic acid 2-methyl ester (49 mg, 0.13 mmol) and carbonyldiimidazole (25 mg, 0.15 mmol) were dissolved in THF (6 ml). After stirring for 1.5 hr at 60° C., the reaction was cooled to RT. Benzylamine (30 μl, 0.27 mmol, 2.1 equiv) was added and stirred for 3 hr. Removal of solvent followed by column chromatography yielded 9mg (15%) of 6-benzylcarbamoyl-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester.

Workup

  1. temperaturethe reaction was cooled to RT
  2. stirringstirred for 3 hr
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-88a918a8ddec44fbba7fb55d8745904d
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07674822B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes