HCID 11166445, compound → HCID 11440720, compound

HRID 560934Notes

Reaction equation

HRID 560934 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[C:6]([O:29]COC)[CH:7]=[CH:8][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=3[F:28])=[O:19])=[CH:13][CH:12]=2)[NH:4][N:3]=1.Cl.CO.C1COCC1>>[NH2:1][C:2]1[C:10]2[C:5](=[C:6]([OH:29])[CH:7]=[CH:8][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=3[F:28])=[O:19])=[CH:13][CH:12]=2)[NH:4][N:3]=1

Participants

3

Reactant 2

HCID 11166445HCID 11166445, compoundHCID 67095823HCID 67095823, compound

Product 1

HCID 11440720HCID 11440720, compoundYield 37.1%

Conditions

Temperature
50 °C

Procedure

A mixture of Example 119B (90 mg) and a 1:1:1 mixture of 3N HCl/methanol/THF (3 mL) was heated to 50° C. for 3 hours, concentrated to half its original volume, and partitioned between saturated NaHCO3 and ethyl acetate. The organic extract was dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane to provide 30 mg of the desired product. MS (ESI(+)) m/e 392 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 2.28 (s, 3H), 4.25 (s, 2H), 6.60 (d, J=5.76 Hz, 2H), 6.82 (m, J=5.09, 3.05 Hz, 1H), 7.11 (m, 2H), 7.33 (d, J=8.48 Hz, 1H), 7.54 (d, J=8.81 Hz, 2H), 8.01 (dd, J=7.97, 2.20 Hz, 1H), 8.51 (d, J=2.71 Hz, 1H), 9.14 (s, 1H), 9.84 (s, 1H), 11.58 (s, 1H).

Workup

  1. concentrationconcentrated to half its original volume
  2. custompartitioned between saturated NaHCO3 and ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-07eae3f378be497cb291b4f67ac41d19
Source dataset
uspto-grants-2011_11
Patent number
US08063091B2

Reaction notes

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