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Trifluoroacetic acid → HCID 21873402, compound

HRID 723354
Notes
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Reaction equation

HRID 723354 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[C:13]1([CH3:27])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1.CO[CH:30](OC)[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])=[CH:35][CH:34]=1.FC(F)(F)C(O)=O>CN(C)C=O.C(OCC)(=O)C>[CH3:44][N:42]([CH3:43])[CH2:41][CH2:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([N:32]2[CH:31]=[CH:30][N:26]([C:23]3[CH:22]=[CH:21][C:20]([O:19][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[CH3:27])=[CH:25][CH:24]=3)[C:1]2=[O:2])=[CH:38][CH:37]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 925054-(o-Tolyloxy)anilineHCID 21873475HCID 21873475, compound

Product 1

HCID 21873402HCID 21873402, compound

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Carbonyldiimidazole (40 mg) was added to a solution of 4-o-tolyloxyphenylamine (50 mg) in dimethylformamide (2 mL) at 0° C. After 30 minutes, (2,2-dimethoxyethyl)-[4-(2-dimethylaminoethoxy)phenyl]amine (67 mg) was added, and the mixture was heated at 80° C. for 2 hours. After cooling to room temperature, trifluoroacetic acid (0.5 mL) was added and the mixture was left to stand for 72 hours. The reaction solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was dried and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 429.52 (C26H27N3O3); MS (ESI): 430 ([M+H]+), was obtained as hydrotrifluoroacetate in this way.

Workup

  1. temperatureAfter cooling to room temperature
  2. waitthe mixture was left
  3. waitto stand for 72 hours
  4. washwashed with saturated sodium bicarbonate solution
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC
  8. customMS (ESI): 430 ([M+H]+), was obtained as hydrotrifluoroacetate in this way

Sources & evidence

ORD record
ord-a46f2375f0a44419bf14d3bde4c87df0
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07141561B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes