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Acetic Acid → N-(4-{2-[4-(4,5-dihydro-1H-imidazol-2-ylamino)phenyl]-ethyl}-1,3-thiazol-2-yl)acetamide

HRID 1246431
Notes
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Reaction equation

HRID 1246431 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1.CS[C:21]1[N:22](C(OCC)=O)[CH2:23][CH2:24][N:25]=1.C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C(O)C>[NH:25]1[CH2:24][CH2:23][N:22]=[C:21]1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 4123199ethyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylateHCID 21914814N-{4-[2-(4-aminophenyl)ethyl]thiazol-2-yl}acetamide

Product 1

HCID 21914923N-(4-{2-[4-(4,5-dihydro-1H-imidazol-2-ylamino)phenyl]-ethyl}-1,3-thiazol-2-yl)acetamideYield 48.8%

Reagents, catalysts & solvents

2
HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of N-(4-(2-(4-aminophenyl)ethyl)-1,3-thiazol-2-yl)acetamide (65 mg) prepared in a similar manner according to Step 6 of Production Example 1, ethyl 2-(methylsulfanyl)-4,5-dihydro-1H-imidazole-1-carboxylate (56 mg), acetic acid (0.1 ml), ethanol (0.9 ml) was stirred at 65° C. for 6 hours, and then refluxed for 5 hours. The reaction mixture was poured into ethyl acetate (5 ml) and saturated aqueous sodium bicarbonate. The precipitated solid was filtered, and the solid was dissolved in 50% methanol/chloroform. The insoluble materials were filtered off and the filtrate was concentrated in vacuo. The solid residue was collected and washed with ethyl acetate to give N-(4-{2-[4-(4,5-dihydro-1H-imidazol-2-ylamino)phenyl]-ethyl}-1,3-thiazol-2-yl)acetamide (40 mg).

Workup

  1. customprepared in a similar manner
  2. temperaturerefluxed for 5 hours
  3. filtrationThe precipitated solid was filtered
  4. dissolutionthe solid was dissolved in 50% methanol/chloroform
  5. filtrationThe insoluble materials were filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe solid residue was collected
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-53881f5a2b0f4f518e3755c160fd0192
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07125901B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes