Water → HCID 86594315, compound

HRID 729729Notes

Reaction equation

HRID 729729 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[C:10](=[CH:19]\[CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)/[C:11]([NH:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)=[O:12])=[CH:6][CH:5]=1)([O-])=O.O.[NH4+].[Cl-]>CCO.C1COCC1.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7](/[C:10](=[CH:19]\[CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)/[C:11]([NH:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)=[O:12])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 10383831HCID 10383831, compound

Product 1

HCID 86594315HCID 86594315, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of (E)-2-(4-nitrophenyl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylacrylamide (EXAMPLE 81, 1.54 g, 4.0 mmol) in EtOH (54 mL) and THF (31 mL) was treated with H2O (13 mL), saturated aqueous NH4Cl (13 mL), and Fe powder (1.49 g, 26.7 mmol). After 4.5 h at 20° C., the reaction mixture was filtered through Celite, washing with CH2Cl2. The combined filtrates were concentrated and the residue was dissolved in CH2Cl2. The CH2Cl2 solution was washed with H2O and dried (MgSO4). Filtration, solvent evaporation, and column chromatography (EtOAc-MeOH, 19:1) gave (E)-2-(4-aminophenyl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylacrylamide; m/z (ES+)=330.1 [M+H]+. A stirred solution of this compound (104 mg, 291 μmol) in anhydrous CH2Cl2 (4 mL) was treated with MeSO2Cl (90 μL, 1165 μmol) and pyridine (94 μL, 1165 μmol). After 16 h, the mixture was diluted with CH2Cl2 (25 mL), before being extracted twice with 2M NaOH. The combined aqueous extracts were washed with Et2O, before being acidified with 12M HCl to pH 1 and extracted twice with CH2Cl2. The combined organic extracts were washed with brine and dried (MgSO4). Filtration and solvent evaporation afforded the title compound: RTB=1.26 min; m/z (ES+)=408.0 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. washwashing with CH2Cl2
  3. concentrationThe combined filtrates were concentrated
  4. dissolutionthe residue was dissolved in CH2Cl2
  5. washThe CH2Cl2 solution was washed with H2O
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration, solvent evaporation, and column chromatography (EtOAc-MeOH, 19:1)

Sources & evidence

ORD record
ord-f03f6a0ee3a746d0a746f97b5f8e439a
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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