Hydrochloric Acid → HCID 21846665, compound

HRID 619643Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[C:19][C:20]4[CH:30]=[CH:29][C:23]([C:24]([O:26]CC)=[O:25])=[CH:22][N:21]=4)[CH:16]=3)[S:11][C:10]([CH3:32])([CH3:31])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:1][CH:2]([CH2:7][CH3:6])[CH2:3][CH2:4][CH2:5][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][C:20]3[CH:30]=[CH:29][C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=3)[CH:16]=2)[S:11][C:10]([CH3:32])([CH3:31])[CH:9]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of ethyl 6-[[4-(4-methylphenyl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-nicotinate (Compound 240, 66.0 mg, 0.15 mmol) in 2.0 mL THF and 2.0 mL EtOH was added NaOH (80.0 mg, 2.0 mmol, 2.0 mL of a 1M aqueous solution). The resulting solution was heated to 45° C. and stirred overnight. Upon cooling to room temperature the reaction mixture was acidified with 10% aqueous HCl and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and dried (Na2SO4) before removing the solvent under reduced pressure to give the title compound as a yellow solid, 50.0 mg (81%). 1H NMR (300 MHz, d6 -acetone) δ: 9.09 (1H, d, J=1.4 Hz), 8.30 (1H, dd, J=2.0, 8.1 Hz), 7.65 (1H, d, J=8.1 Hz), 7.46 (2H, s), 7.24 (5H, m), 5.94 (1H, s), 2.37 (3H, s), 1.48 (6H, s).

Workup

temperatureUpon cooling to room temperature the reaction mixture
extractionextracted with EtOAc
washThe combined organic layers were washed with H2O, saturated aqueous NaCl
dry with materialdried (Na2SO4)
custombefore removing the solvent under reduced pressure

Sources & evidence

ORD record: ord-08101e10436a4350bb89e5a49ea4256a
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05958954

Reaction notes

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