Hydrochloric Acid → HCID 67040321, compound

HRID 605209Notes

Reaction equation

HRID 605209 reaction equation
ClC(Cl)(Cl)COC(=O)[NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:31])[NH:21][C:22]3[S:23][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[N:25][N:26]=3)=[CH:16][C:15]=2[NH:32][C:33]2[C:34]3[CH:42]=[CH:41][C:40]([CH:43]([CH3:45])[CH3:44])=[N:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[CH:9][CH:8]=1.[OH-].[Na+].Cl>O1CCCC1.O>[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH:21][C:22]3[S:23][C:24]([C:27]([CH3:28])([CH3:29])[CH3:30])=[N:25][N:26]=3)=[O:31])=[CH:16][C:15]=2[NH:32][C:33]2[C:34]3[CH:42]=[CH:41][C:40]([CH:43]([CH3:45])[CH3:44])=[N:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67040891HCID 67040891, compound

Product 1

HCID 67040321HCID 67040321, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product of Example 181B in tetrahydrofuran and water (1:1) was added 1 M NaOH (5 equiv). The solution was heated at 60° C. for 40 minutes, cooled, adjusted to pH 6 with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated under vacuum. The resultant residue was purified by silica gel chromatography eluting with 4% methanol in dichloromethane to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.34 (d, J=6.62 Hz, 6 H) 1.41 (s, 9 H) 3.16-3.30 (m, 1 H) 5.64 (s, 1 H) 6.65 (d, J=8.46 Hz, 2 H) 6.85 (d, J=8.46 Hz, 1 H) 7.15 (d, J=8.46 Hz, 2 H) 7.65 (d, J=8.46 Hz, 1 H) 7.94 (dd, J=8.46, 1.84 Hz, 1 H) 8.10 (d, J=1.47 Hz, 1 H) 8.59 (s, 1 H) 8.89 (d, J=8.82 Hz, 1 H) 10.15 (s, 1 H) 12.85 (s, 1 H).

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe resultant residue was purified by silica gel chromatography
  7. washeluting with 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-24aab925a6d0486098d442be8721319c
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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