Hydrochloric Acid → HCID 86711510, compound

HRID 1771389Notes

Reaction equation

O=[C:2]([CH:6]1[CH2:10][CH2:9][O:8][CH2:7]1)[CH2:3][C:4]#[N:5].Cl.Cl.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1.[OH-].[Na+]>CCO>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:4]([NH2:5])=[CH:3][C:2]([CH:6]3[CH2:10][CH2:9][O:8][CH2:7]3)=[N:22]2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-oxo-3-(tetrahydrofuran-3-yl)propanenitrile (718 mg, 4.64 mmol) in EtOH (20 mL) was added conc. hydrochloric acid (0.387 mL, 4.64 mmol) and (4-methoxyphenyl)hydrazine hydrochloride (737 mg, 4.22 mmol). The reaction mixture was heated to 80° C. for 4 hr and was then cooled to RT and adjusted to pH8 by the addition of aq NaOH (2M, <5 mL). The resulting mixture was partitioned between water (20 mL) and Et2O (25 mL) and the aq layer was separated and extracted with ether (25 mL). The combined organic extracts were dried and evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, 40 g, 0-5% MeOH in DCM, gradient elution) to afford the title compound, Intermediate A12, as a pale orange solid (503 mg, 45%); Rt 1.04 min (Method 2); m/z 260 (M+H)+, (ES+).

Workup

temperaturewas then cooled to RT
customThe resulting mixture was partitioned between water (20 mL) and Et2O (25 mL)
customthe aq layer was separated
extractionextracted with ether (25 mL)
customThe combined organic extracts were dried
customevaporated in vacuo
customthe residue was purified by flash column chromatography (SiO2, 40 g, 0-5% MeOH in DCM, gradient elution)

Sources & evidence

ORD record: ord-202cc32f718249f98e7d92cd80a4791d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249125B2

Reaction notes

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