Sodium 2-propanethiolate → HCID 67436380, compound

HRID 1663415Notes

Reaction equation

HRID 1663415 reaction equation
CC([S-])C.[Na+].[CH3:6][C:7]([CH:13]1[C:22]2[CH:23]=[N:24][C:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)=[O:34])=[CH:29][CH:28]=3)=[CH:26][C:21]=2[O:20][C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]1=2)([CH3:12])[C:8]([O:10]C)=[O:9]>CN(C=O)C>[CH3:12][C:7]([CH:13]1[C:22]2[CH:23]=[N:24][C:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([N:35]4[CH2:36][CH2:37][O:38][CH2:39][CH2:40]4)=[O:34])=[CH:29][CH:28]=3)=[CH:26][C:21]=2[O:20][C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]1=2)([CH3:6])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 3470666Sodium 2-propanethiolate3×HCID 67436421HCID 67436421, compound

Product 1

HCID 67436380HCID 67436380, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium 2-propanethiolate (58.5 mg, 0.596 mmol) was added to a solution of methyl 2-methyl-2-(3-(4-(morpholine-4-carbonyl)phenyl)-10H-chromeno[3,2-c]pyridin-10-yl)propanoate (140.9 mg, 0.298 mmol) in DMF (5 mL) and the mixture was heated to 50° C. After 1 h at 50° C., additional sodium 2-propanethiolate (58.5 mg) was added. The mixture was stirred at 50° C. overnight. Another portion of sodium 2-propanethiolate (200 mg) was added. After another hour at 50° C., the mixture was quenched with saturated NH4Cl (20 mL) and extracted with EtOAc (4×20 mL). The combined extracts were washed with brine (5 mL), dried (MgSO4) and concentrated to give 2-methyl-2-(3-(4-(morpholine-4-carbonyl)phenyl)-10H-chromeno[3,2-c]pyridin-10-yl)propanoic acid as a solid (145.5 mg). MS (ES+) m/z: 459 (M+H); HPLC retention time: 3.51 min (Analytical HPLC Method D).

Workup

  1. waitAfter another hour at 50° C.
  2. customthe mixture was quenched with saturated NH4Cl (20 mL)
  3. extractionextracted with EtOAc (4×20 mL)
  4. washThe combined extracts were washed with brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bcc217d495a449ec80c0e22f47ee024e
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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