Hydrochloric Acid → HCID 69217594, compound

HRID 272682Notes

Reaction equation

HRID 272682 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[C:17](=[O:18])[NH:16][C:15]4[CH:19]=[C:20]([C:23]([O:25]C)=[O:24])[CH:21]=[CH:22][C:14]=4[NH:13][C:12]=3[CH:27]=2)[CH:5]=[CH:4][N:3]=1.[Li+].[OH-].Cl>O.C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[C:17](=[O:18])[NH:16][C:15]4[CH:19]=[C:20]([C:23]([OH:25])=[O:24])[CH:21]=[CH:22][C:14]=4[NH:13][C:12]=3[CH:27]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69219987HCID 69219987, compound

Product 1

HCID 69217594HCID 69217594, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 69B (60 mg, 0.17 mmol) and LiOH (20 mg, 0.85 mmol) in water (5 mL) and THF (5 mL) was heated to reflux until a homogeneous solution formed, adjusted to pH 5 with 10% HCl, and extracted with ethyl acetate several times. The combined extracts were washed with brine, dried (CaCl2), filtered, and concentrated under vacuum to provide 47 mg (80%) of the desired product. MS (DCI) m/e 349 (M)+; 1H NMR (500 MHz, DMSO-d6) δ 10.03 (s, 1H), 8.42 (s, 1H), 8.36 (d, J=5.3 Hz, 1H), 7.85 (d, J=8.4 Hz, 1H), 7.62 (d, J=5.3 Hz, 1H), 7.60 (d, J=1.6 Hz, 1H), 7.55 (dd, J=8.4, 1.9 Hz, 1H), 7.45 (s, 1H), 7.24 (d, J=1.6 Hz, 1H), 7.37 (dd, J=8.1, 1.9 Hz, 1H), 7.05 (d, J=8.4 Hz, 1H).

Workup

  1. temperatureto reflux until a homogeneous solution
  2. customformed
  3. extractionextracted with ethyl acetate several times
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (CaCl2)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3f1a41e97c2c424bb93d2226465a12b1
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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