Methanol → HCID 67883923, compound

HRID 1656540Notes

Reaction equation

HRID 1656540 reaction equation
[N+:1]([C:4]1[CH:41]=[CH:40][C:7]([CH2:8][NH:9][S:10]([NH:13][C:14]2[S:18][C:17]([C:19]3[N:20]([CH2:26][C:27]([NH:29][CH:30]([CH:37]([CH3:39])[CH3:38])[C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])=[O:28])[C:21](=[O:25])[CH:22]=[CH:23][N:24]=3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[C:42](OC(=O)C)(=[O:44])[CH3:43].CO>C(O)(=O)C.[Fe]>[C:42]([NH:1][C:4]1[CH:41]=[CH:40][C:7]([CH2:8][NH:9][S:10]([NH:13][C:14]2[S:18][C:17]([C:19]3[N:20]([CH2:26][C:27]([NH:29][CH:30]([CH:37]([CH3:39])[CH3:38])[C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])=[O:28])[C:21](=[O:25])[CH:22]=[CH:23][N:24]=3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:44])[CH3:43]

Participants

6

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 67883659HCID 67883659, compound

Product 1

HCID 67883923HCID 67883923, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-[5-(4-nitrobenzylaminosulfonylamino)-6-oxo-2-thienyl-1,6-dihydro-1-pyrimidinyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.431 g) in acetic acid (12 mL) was added acetic anhydride (0.265 mL), followed by iron powder (0.783 g). The reaction was stirred at room temperature overnight. Methanol was added and the reaction mixture filtered through diatomaceous earth to remove excess iron. Ethyl acetate was added and the resultant solution washed (water (twice), brine), dried (MgSO4) and evaporated. The crude material was purified by chromatography, with dichloromethane:methanol (gradient, 99.5:0.5, 98:2) as the eluent, to provide the title compound (0.247 g); TLC: Rf =0.27, dichloromethane:methanol (98:2); NMR: 0.87-0.97 (m,6), 2.17-2.30 (m,1), 3.32 (s,3), 4.02 (d,2), 4.73-4.77 (m,1) 4.77-4.93 (m,2), 7.13-7.20 (m,3), 7.33 (d,1), 7.47 (d,2), 7.80-7.87 (m,1), 7.91 (s,1), 7.97-8.03 (m,1), 9.04 (d,1), 9.09 (s,1), 9.87 (s,1); MS: m/z=629(M+1).

Workup

  1. filtrationthe reaction mixture filtered through diatomaceous earth
  2. customto remove excess iron
  3. additionEthyl acetate was added
  4. washthe resultant solution washed (water (twice), brine),
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude material was purified by chromatography, with dichloromethane

Sources & evidence

ORD record
ord-e838ef589ef645dc99036621d6d0f3e8
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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