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tert-Butoxy bis(dimethylamino)methane → 4-(3-Dimethylamino-2-phenyl-acryloyl)-1H-pyrrole-2-carboxylic acid benzylamide

HRID 47259
Notes
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Reaction equation

HRID 47259 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[NH:12][CH:13]=[C:14]([C:16](=[O:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25](OC(C)(C)C)(N(C)C)[N:26]([CH3:28])[CH3:27]>C1COCC1>[CH2:1]([NH:8][C:9]([C:11]1[NH:12][CH:13]=[C:14]([C:16](=[O:24])[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:25][N:26]([CH3:28])[CH3:27])[CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 121254174-Phenylacetyl-1H-pyrrole-2-carboxylic acid benzylamide

Product 1

HCID 694268864-(3-Dimethylamino-2-phenyl-acryloyl)-1H-pyrrole-2-carboxylic acid benzylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 2 (1 equivalent) in THF, at ambient temperature, was added (Me2N)2CHOt-Bu (3 equivalents). After 24 hours, the solvent was evaporated and the crude product 3 was utilized without purification. 1H NMR (CDCl3) δ4.4 (s, 2H), 4.8 (s, NH), 6.8-7.4 (m, 13H).

Workup

  1. customthe solvent was evaporated
  2. customthe crude product 3 was utilized without purification

Sources & evidence

ORD record
ord-7f59283adf5042a7898d3252250cc88f
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06699865B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes