Hydrochloric Acid → HCID 67041044, compound

HRID 605207Notes

Reaction equation

HRID 605207 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:32])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=3)=[CH:16][C:15]=2[NH:33][C:34]2[C:35]3[CH:43]=[CH:42][C:41]([CH:44]([CH3:46])[CH3:45])=[N:40][C:36]=3[N:37]=[CH:38][N:39]=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]([C:28]([F:31])([F:29])[F:30])=[CH:24][N:23]=3)=[O:32])=[CH:16][C:15]=2[NH:33][C:34]2[C:35]3[CH:43]=[CH:42][C:41]([CH:44]([CH3:46])[CH3:45])=[N:40][C:36]=3[N:37]=[CH:38][N:39]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86615558HCID 86615558, compound

Product 1

HCID 67041044HCID 67041044, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product of Example 175B 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 crude product 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=6.62 Hz, 6 H) 3.15-3.29 (m, 1 H) 5.63 (s, 2 H) 6.65 (d, J=8.46 Hz, 2 H) 6.84 (d, J=8.46 Hz, 1 H) 7.16 (d, J=8.46 Hz, 2 H) 7.64 (d, J=8.46 Hz, 1 H) 7.90 (d, J=6.99 Hz, 1 H) 8.06 (s, 1 H) 8.23 (dd, J=8.82, 1.47 Hz, 1 H) 8.39 (d, J=8.82 Hz, 1 H) 8.59 (s, 1 H) 8.76 (s, 1 H) 8.89 (d, J=8.46 Hz, 1 H) 10.14 (s, 1 H) 11.20 (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 crude product was purified by silica gel chromatography
  7. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-bcc51f2a03a6466595325322892a4bca
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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