Hydrochloric Acid → HCID 66696644, compound

HRID 1672582Notes

Reaction equation

HRID 1672582 reaction equation
C([O:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[N:15]=C(C2C=CC=CC=2)C2C=CC=CC=2)[O:7][CH2:6]1)(=O)C.Cl.O.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(Cl)Cl>[NH2:15][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[CH2:14][CH:5]([OH:4])[CH2:6][O:7]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 87113368HCID 87113368, compound

Product 1

HCID 66696644HCID 66696644, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 51D (504 mg, 1.36 mmol) in THF (5 mL) was stirred at room temperature, followed by addition of 6N aq HCl (3.4 mL, 6.8 mmol). After 10 min water (20 mL) and CH2Cl2 (10 mL) were added and the layers separated. The aqueous layer was washed with CH2Cl2 (5 mL). The aqueous layer was then neutralized with saturated NaHCO3 solution and extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was taken up in MeOH (5 mL) and K2CO3 (938 mg, 6.78 mmol) was added. After 20 min CH2Cl2 (50 mL) was added and the mixture was filtered and concentrated in vacuo. The crude product was purified by flash chromatography (50%-100% EtOAc/hexanes) to afford 145 mg (65%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 6.73 (t, J=8.0, 1H), 6.18 (dd, J=7.9, 1.1, 1H), 5.98 (dd, J=8.1, 1.0, 1H), 5.06 (d, J=4.2, 1H), 4.81 (bs, 2H), 4.01-3.92 (m, 2H), 3.63 (dd, J=11.0, 8.1, 1H), 2.64 (dd, J=16.9, 6.2, 1H), 2.23 (dd, J=16.1, 6.7, 1H). MS (ESI+) m/z 166 (M+H).

Workup

  1. customthe layers separated
  2. washThe aqueous layer was washed with CH2Cl2 (5 mL)
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationthe mixture was filtered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography (50%-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ca86d87ec7cd46cf98aeafe1944aa782
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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