Tetrahydrofuran → HCID 58409912, compound

HRID 1844889Notes

Reaction equation

HRID 1844889 reaction equation
O=[C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:5]=[C:4]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)O1.[H-].[Na+].[CH2:23]1[CH2:27]O[CH2:25][CH2:24]1>>[N:10]1([C:6]2[CH:5]=[C:4]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:6]3[C:5]4[C:24](=[CH:23][CH:27]=[CH:16][CH:4]=4)[CH2:25][C:2]=3[C:7]=2[C:8]#[N:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11449042HCID 11449042, compound

Product 1

HCID 58409912HCID 58409912, compound

Procedure

A mixture of 2-oxo-4-(piperidin-1-yl)-6-(thiophen-2-yl)-2H-pyran-3-carbonitrile (286 mg), indanone-2 (132 mg) and NaH (41 mg) in THF was stirred for <5 min. After completion, the reaction solvent was evaporated under vacuum to dryness and crude solid was quenched with ice water and subsequently neutralized with dil. HCl, finally purified by column chromatography using ethylacetate-hexane as eluent. White solid; mp 148-150° C.; FAB MS 357 (M++1); IR (KBr) 2215 cm−1 (CN), 1H NMR (200 MHz, CDCl3) δ 1.60-1.64 (m, 2H, CH2), 1.79-1.82 (m, 4H, 2CH2), 3.20-3.25 (m, 4H, 2CH2), 4.10 (s, 2H, CH2), 6.92 (s, 1H, ArH), 7.10-7.24 (m, 5H, ArH & CH), 7.49-7.54 (m, 2H, ArH & CH); HRMS calcd. for C23H20N2S 356.13472. Found 356,13580.

Workup

  1. customAfter completion, the reaction solvent was evaporated under vacuum to dryness
  2. customcrude solid was quenched with ice water
  3. customfinally purified by column chromatography

Sources & evidence

ORD record
ord-ac844d0fc3b64b0c9725a29865a06513
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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