Hydrochloric Acid → HCID 46846701, compound

HRID 2039658Notes

Reaction equation

HRID 2039658 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[N:26]=[C:25]([C:27]([O:29]CC)=[O:28])[CH:24]=[CH:23][CH:22]=3)[N:20]=2)=[CH:5][CH:4]=1.[OH-].[K+].Cl>C(O)C.O>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[N:26]=[C:25]([C:27]([OH:29])=[O:28])[CH:24]=[CH:23][CH:22]=3)[N:20]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 46846700HCID 46846700, compound

Product 1

HCID 46846701HCID 46846701, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a slurry of ethyl 6-(2-(4-methoxydibenzo[b,d]furan-1-yl)thiazol-4-yl)picolinate (50 mg, 0.116 mmol) in ethanol (5 mL), potassium hydroxide (30 mg, 0.535 mmol) in water (0.5 mL) was added. The reaction slurry was stirred at room temperature for 2 h. Subsequently the reaction mixture was poured into water acidified with 1N HCl to a pH of 3-4; the precipitated solid was filtered and washed with ether and hexane. Yield—42%; Rf 0.23 (Chloroform:Methanol (8.5:1.5); HPLC (purity): 96%; 1H-NMR (CDCl3) δ: 4.15 (s, 3H), 7.09 (d, 1H), 7.29-7.32 (m, 1H), 7.51-7.55 (m, 2H), 8.08-8.12 (m, 1H), 8.24 (d, 1H), 8.56 (d, 1H), 8.75 (d, 1H); MS m/z: 403.1 (M+1).

Workup

  1. filtrationthe precipitated solid was filtered
  2. washwashed with ether and hexane

Sources & evidence

ORD record
ord-99113c55e3b848f09b681065d0997c79
Source dataset
uspto-grants-2013_11
Patent number
US08580795B2

Reaction notes

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