Hydrochloric Acid → HCID 21846684, compound

HRID 619644Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[C:20][C:21]4[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][N:22]=4)[CH:17]=3)[S:12][C:11]([CH3:33])([CH3:32])[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[OH-].[Na+].Cl>C1COCC1.CCO>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][CH2:20][C:21]4[CH:31]=[CH:30][C:24]([C:25]([OH:27])=[O:26])=[CH:23][N:22]=4)[CH:17]=3)[S:12][C:11]([CH3:32])([CH3:33])[CH:10]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 6-[[4-(4-ethylphenyl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-nicotinate (Compound 241, 110.0 mg, 0.24 mmol) in 3.0 mL THF and 3.0 mL EtOH was added NaOH (120.0 mg, 3.0 mmol, 3.0 mL of a 1M aqueous solution). This mixture was heated to 40° C. for 1 hour, cooled to room temperature, and the resulting solution was stirred overnight. 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 100 mg (96%) of the title compound as a colorless solid. 1H NMR (300 MHz, d6 -acetone) δ: 9.08 (1H, d, J=2.0 Hz), 8.30 (1H, dd, J=2.2, 8.2 Hz), 7.66 (1H, d, J=8.2 Hz), 7.46 (2H, s), 7.31-7.21 (5H, m), 5.95 (1H, s), 2.69 (2H, q, J=7.6 Hz), 1.48 (6H, s), 1.25 (3H, t, J=7.6 Hz).

Workup

temperaturecooled to room temperature
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-6f1c58e45e7440c0b0396435bef9897f
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05958954

Reaction notes

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