Methanol → HCID 21914919, compound

HRID 2117907Notes

Reaction equation

HRID 2117907 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]([NH:23][C:24](=[O:26])[CH3:25])[S:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1)([O-])=O.[N+](C1C=CC(/C=C\C2N=C(NC(=O)C)SC=2C2C=CC=CC=2)=CC=1)([O-])=O.CO.C1COCC1>[C].[Pd].CC(O)=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:23][C:24](=[O:26])[CH3:25])[S:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 21915123HCID 21915123, compoundHCID 86595600HCID 86595600, compound

Product 1

HCID 21914919HCID 21914919, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of N-{4-[(E)-2-(4-nitrophenyl)vinyl]-5-phenyl-1,3-thiazol-2-yl}acetamide and N-{4-[(Z)-2-(4-nitrophenyl)vinyl]-5-phenyl-1,3-thiazol-2-yl}acetamide (E:Z=2:1) (600 mg), 10% palladium carbon (657 mg), MeOH (6 ml), THF (6 ml) and AcOH (1 ml) were combined. The reaction mixture was stirred under 3 atm H2 at r.t. for 3.5 hours, and filtered through a celite pad. The filtrate was concentrated in vacuo. 1N—NaOH was added to the residue, and the mixture was extracted with AcOEt. The organic layer was washed with water and brine, dried over MgSO4, and concentrated in vacuo to give N-{4-[2-(4-aminophenyl)ethyl]-5-phenyl-1,3-thiazol-2-yl}acetamide (528.6 mg) as a pale brown amorphous substance.

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationThe filtrate was concentrated in vacuo
  3. addition1N—NaOH was added to the residue
  4. extractionthe mixture was extracted with AcOEt
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00ba86cdc26f4af3a1ff1776106497ba
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

Loading…