Hydrochloric Acid → HCID 67436586, compound

HRID 1663404Notes

Reaction equation

HRID 1663404 reaction equation
CC([S-])C.[Na+].[CH3:6][N:7]([CH3:39])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]3[O:22][C:23]4[C:28]([CH:29]([C:30]5([C:34]([O:36]CC)=[O:35])[CH2:33][CH2:32][CH2:31]5)[C:19]3=[CH:18][CH:17]=2)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:12][CH:11]=1)=[O:9].Cl.C(OCC)(=O)C>CN(C=O)C>[CH3:6][N:7]([CH3:39])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]3[O:22][C:23]4[C:28]([CH:29]([C:30]5([C:34]([OH:36])=[O:35])[CH2:33][CH2:32][CH2:31]5)[C:19]3=[CH:18][CH:17]=2)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:12][CH:11]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 3470666Sodium 2-propanethiolateHCID 67436964HCID 67436964, compound

Product 1

HCID 67436586HCID 67436586, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium propane-2-thiolate (172 mg, 1.75 mmol) was added to a solution of the product from Step 2 (80 mg, 0.175 mmol) in DMF (5 mL) at room temperature. After 15 h at 60° C., the mixture was cooled to room temperature and adjusted pH2-3 with 1 N aqueous HCl. After addition of ethyl acetate (100 mL), the mixture was washed with water (10 mL), brine (10 mL), dried (MgSO4) and concentrated. Purification by preparative HPLC gave the desired 1-(2-(4-(dimethylcarbamoyl)phenyl)-5H-chromeno[2,3-b]pyridin-5-yl)cyclobutanecarboxylic acid (45 mg, 60%). MS (ES+) m/z: 429 (M+H).

Workup

  1. washthe mixture was washed with water (10 mL), brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-2246bf0041304e3f8065d607681d97a8
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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