Hydrochloric Acid → HCID 9885053, compound

HRID 985489Notes

Reaction equation

HRID 985489 reaction equation
[OH-].[Na+].[CH3:3][NH:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]3[C:21]([CH2:22][CH2:23][C:24]([O-:26])=[O:25])=[CH:20][S:19][C:18]=3[CH:27]=2)[CH:8]=[CH:7][CH:6]=1.C1COCC1.Cl>O.C(OCC)(=O)C>[CH3:3][NH:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]3[C:21]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:20][S:19][C:18]=3[CH:27]=2)[CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22507070HCID 22507070, compound

Product 1

HCID 9885053HCID 9885053, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1N NaOH (10 ml) was added to a solution of 3-(6-{2-[6-(Methylamino)-2-pyridyl]ethoxy}benzo[b]thiophen-3-yl)propanoate and THF (10 ml ). The reaction was stirred at room temperature for 16 h. The mixture was diluted with water and ethyl acetate. The separated aqueous layer was neutralized with 1 N HCl to pH=6.5. The resulting precipitate was filtered, washed with distilled water, and dried to yield 74 mg (55%) of 3-(6-{2-[6-(methylamino)-2-pyridyl]ethoxy}benzo[b]thiophen-3-yl)propanoic acid as a white solid. NMR 1H DMSO-d6 δ: 7.67 (d, 1H, J=8.0 Hz), 7.58 (d, 1H, J=2.4 Hz), 7.31 (dd, 1H, J=7.2, 8.0 Hz), 7.18 (s, 1H), 7.00 (dd, 1H, J=2.4, 8.0 Hz), 6.45 (d, 1H, J=7.2 Hz), 6.37 (m, 1H), 6.27 (d, 1H, J=8.0 Hz), 4.36 (t, 2H, J=6.4 Hz), 2.99 (t, 2H, J=6.4 Hz), 2.90 (d, 3H, J=8.0 Hz), 2.64 (t, 2H, J=6.4 Hz). Mass Spectrum (LCMS, ESI) calculate for C19H21N2O3S 357.1 (M+H) found: 357.3.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with distilled water
  3. customdried

Sources & evidence

ORD record
ord-4545375751424655baac534bc8c8daa5
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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