Hydrochloric Acid → HCID 67040371, compound

HRID 605206Notes

Reaction equation

HRID 605206 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:29])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=3)=[CH:16][C:15]=2[NH:30][C:31]2[C:32]3[CH:40]=[CH:39][C:38]([CH:41]([CH3:43])[CH3:42])=[N:37][C:33]=3[N:34]=[CH:35][N:36]=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[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=3)=[O:29])=[CH:16][C:15]=2[NH:30][C:31]2[C:32]3[CH:40]=[CH:39][C:38]([CH:41]([CH3:43])[CH3:42])=[N:37][C:33]=3[N:34]=[CH:35][N:36]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67041009HCID 67041009, compound

Product 1

HCID 67040371HCID 67040371, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product of Example 174B 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 2% methanol in dichloromethane to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.34 (d, J=6.99 Hz, 6 H) 3.15-3.29 (m, J=6.89, 6.89, 6.89, 6.89 Hz, 1 H) 5.62 (s, 2 H) 6.65 (d, J=8.46 Hz, 2 H) 6.83 (d, J=8.46 Hz, 1 H) 7.15 (d, J=8.46 Hz, 2 H) 7.64 (d, J=8.46 Hz, 1 H) 7.79 (dt, J=8.64, 2.94 Hz, 1 H) 7.87 (dd, J=8.46, 1.84 Hz, 1 H) 8.04 (d, J=1.84 Hz, 1 H) 8.20 (dd, J=9.19, 4.04 Hz, 1 H) 8.38 (d, J=2.94 Hz, 1 H) 8.58 (s, 1 H) 8.89 (d, J=8.46 Hz, 1 H) 10.13 (s, 1 H) 10.85 (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 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-5b93b497ded44ec9a6bdaa33eea85a84
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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