Ethanol → HCID 67287176, compound

HRID 1626534Notes

Reaction equation

HRID 1626534 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:35])[NH:20][CH2:21][CH2:22][C:23]3[C:24]([N:32]([CH3:34])[CH3:33])=[N:25][C:26]([CH:29]4[CH2:31][CH2:30]4)=[CH:27][CH:28]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:36]([O:38]CC)=[O:37].[OH-].[Na+].C(O)C>O1CCCC1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:35])[NH:20][CH2:21][CH2:22][C:23]3[C:24]([N:32]([CH3:34])[CH3:33])=[N:25][C:26]([CH:29]4[CH2:31][CH2:30]4)=[CH:27][CH:28]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:36]([OH:38])=[O:37]

Participants

7

Reactant 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 67287554HCID 67287554, compound

Product 1

HCID 67287176HCID 67287176, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 6-chloro-7-(4-(2-(6-cyclopropyl-2-(dimethylamino)pyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylate (77 mg, 0.14 mmol) was diluted with terahydrofuran (1 mL) followed by the addition of aq. NaOH (341 μL, 0.68 mmol) and ethanol (500 μL). After stirring for 2 hours, the reaction was diluted with ethyl acetate and 2N aqueous HCl. The pH of the aqueous layer was adjusted to 6 with 1N aqueous NaOH and extracted with ethyl acetate. The ethyl acetate layer was dried over MgSO4, filtered and concentrated to yield 6-chloro-7-(4-(2-(6-cyclopropyl-2-(dimethylamino)pyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid (70 mg, 0.13 mmol, 96% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5e26af7640b6462a889ea48ed8ed25a6
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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