Hydrochloric Acid → HCID 67436084, compound

HRID 1663408Notes

Reaction equation

HRID 1663408 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH3:34])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[C:17]3[O:19][C:20]4[C:25]([CH:26]([C:27]5([C:30]([O:32]C)=[O:31])[CH2:29][CH2:28]5)[C:16]3=[CH:15][CH:14]=2)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:9][CH:8]=1)=[O:6].Cl.C(OCC)(=O)C>CO>[CH3:3][N:4]([CH3:34])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[C:17]3[O:19][C:20]4[C:25]([CH:26]([C:27]5([C:30]([OH:32])=[O:31])[CH2:29][CH2:28]5)[C:16]3=[CH:15][CH:14]=2)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:9][CH:8]=1)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67436158HCID 67436158, compound

Product 1

HCID 67436084HCID 67436084, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A 1 N aqueous solution of NaOH (0.5 mL, 0.500 mmol) was added to a solution of the product from Step 4 (11 mg, 0.026 mmol) in MeOH (1 mL) at room temperature. The mixture was heated to 60° C. for 3 h, cooled to room temperature and adjusted pH2-3 with 1 N aqueous HCl. Following addition of ethyl acetate (60 mL), the mixture was washed with brine (10 mL), dried (MgSO4) and concentrated to give 1-(2-(4-(dimethylcarbamoyl)phenyl)-5H-chromeno[2,3-b]pyridin-5-yl)cyclopropanecarboxylic acid as crude material (11 mg), which was taken to the next step directly. MS (ES+) m/z: 415 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. washthe mixture was washed with brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2112764aff914254be51f370cf17334b
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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