Acetic Acid → HCID 24993422, compound

HRID 1673232Notes

Reaction equation

HRID 1673232 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([NH:26][C:27]([NH:29][NH2:30])=[O:28])[CH2:24][C:23]([CH3:32])([CH3:31])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.[C:33](O)(=O)C.C(N)=N.CC(O)=O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([N:26]4[CH:33]=[N:30][NH:29][C:27]4=[O:28])[CH2:24][C:23]([CH3:32])([CH3:31])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 160693Formamidine acetateHCID 67019956HCID 67019956, compound

Product 1

HCID 24993422HCID 24993422, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product of Step B (0.14 mmol) and formamidine acetate (72 mg, 0.70 mmol) in 5.0 mL of DMF was allowed to stir at rt for 2 h. AcOH (40 μL, 0.70 mmol) was then added. The resulting mixture was stirred at 80° C. for 16 h. After cooling to rt, the reaction mixture was diluted with EtOAc (20 mL) and washed with brine (3×20 mL). The organic phase was separated, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+S cartridges using 1:99 v/v CH3OH/CH2Cl2 as the eluant afforded the title compound: 1H NMR δ 1.53 (s, 3H), 1.62 (s, 3H), 2.18 (t, J=12.7, 1H), 2.36 (dd, J=6.3, 13.1, 1H), 5.56 (m, 1H), 6.95 (d, J=8.3, 2H), 7.16-7.38 (m, 7H), 10.1 (br. s, 1H).

Workup

  1. stirringThe resulting mixture was stirred at 80° C. for 16 h
  2. temperatureAfter cooling to rt
  3. washwashed with brine (3×20 mL)
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3785e41574774284a4f31e7a15af970c
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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