Hydrochloric Acid → HCID 67040386, compound

HRID 605185Notes

Reaction equation

HRID 605185 reaction equation
C1C2C(COC(=O)[NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([C:31](=[O:42])[NH:32][C:33]5[S:34][C:35]([C:38]([F:41])([F:40])[F:39])=[N:36][N:37]=5)=[CH:27][C:26]=4[NH:43][C:44]4[C:45]5[CH:53]=[CH:52][C:51]([CH:54]([CH3:56])[CH3:55])=[N:50][C:46]=5[N:47]=[CH:48][N:49]=4)=[CH:20][CH:19]=3)C3C(=CC=CC=3)C=2C=CC=1.O.[OH-].[Li+].Cl>O1CCOCC1.O.C(OCC)(=O)C>[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([S:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([NH:32][C:33]3[S:34][C:35]([C:38]([F:41])([F:40])[F:39])=[N:36][N:37]=3)=[O:42])=[CH:27][C:26]=2[NH:43][C:44]2[C:45]3[CH:53]=[CH:52][C:51]([CH:54]([CH3:56])[CH3:55])=[N:50][C:46]=3[N:47]=[CH:48][N:49]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67040582HCID 67040582, compound

Product 1

HCID 67040386HCID 67040386, compoundYield 69.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of the product of Example 154C (114 mg, 0.1416 mmol) in 1,4-dioxane (4 mL) was treated with a solution of lithium hydroxide monohydrate (11.9 mg, 0.2833 mmol) in water (2 mL) at ambient temperature, then heated at 65° for 30 minutes. The reaction was cooled to room temperature, diluted with ethyl acetate (100 mL) and water (50 mL), adjusted the aqueous pH to 5-6 with 1N aqueous hydrochloric acid, and separated the layers. The organic phase was washed with water (2×25 mL) and brine (25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation in vacuo. Trituration of the residue with 3% methanol/methylene chloride afforded the title compound as a light yellow solid (57 mg, 69%). 1H NMR (300 MHz, DMSO-d6/TFA) δ ppm: 1.35 (d, J=6.62 Hz, 6 H) 3.08-3.51 (m, 1 H) 7.25 (d, J=8.46 Hz, 1 H) 7.39 (d, J=8.46 Hz, 2 H) 7.55 (d, J=8.82 Hz, 2 H) 7.94 (d, J=8.82 Hz, 1 H) 8.18 (dd, J=8.46, 2.21 Hz, 1 H) 8.27 (d, J=1.84 Hz, 1 H) 8.99 (s, 1 H) 9.10 (d, J=8.82 Hz, 1 H); MS (ESI+) m/z 583 (M+H)+, (ESI−) m/z 581 (M−H)−.

Workup

  1. temperatureheated at 65° for 30 minutes
  2. customseparated the layers
  3. washThe organic phase was washed with water (2×25 mL) and brine (25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation in vacuo

Sources & evidence

ORD record
ord-f452fd4553c145e89c45b932ccffe5d1
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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