1-Oxaspiro[2.5]octane → HCID 86641450, compound

HRID 1189944Notes

Reaction equation

HRID 1189944 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][CH2:10][NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH:5]=[CH:6][CH:7]=1.[O:18]1[C:20]2([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:19]1>CCO.O>[F:16][C:13]([F:14])([F:15])[C:12]([NH:11][CH2:10][C:9]#[C:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:19][C:20]2([OH:18])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:3]=1)=[O:17]

Participants

4

Reactant 2

HCID 91001-Oxaspiro[2.5]octaneHCID 86641449HCID 86641449, compound

Product 1

HCID 86641450HCID 86641450, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of N-(3-(3-aminophenyl)prop-2-ynyl)-2,2,2-trifluoroacetamide (0.75 g, 3.09 mmol) and 1-oxaspiro[2.5]octane (1.2 g, 9.2 mmol) in EtOH:H2O (9:1) was stirred under reflux for 36 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (20% to 30% EtOAc—hexanes gradient) gave 2,2,2-trifluoro-N-(3-(3-((1-hydroxycyclohexyl)methylamino)phenyl)prop-2-ynyl)acetamide as an off white solid. Yield (0.48 g, 43%); 1H NMR (400 MHz, DMSO-d6) δ 7.28 (s, 1H), 7.00 (t, J=7.6 Hz, 1H), 6.53-6.51 (m, 2H), 6.39 (d, J=7.6 Hz, 1H), 5.28 (t, J=5.6 Hz, 1H), 4.18 (s, 1H), 4.01 (s, 2H), 2.88 (d, J=5.6 Hz, 2H), 1.60-1.47 (m, 4H), 1.39-1.34 (m, 4H), 1.22-1.14 (m, 2H).

Workup

  1. temperatureunder reflux for 36 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customPurification by column chromatography (20% to 30% EtOAc—hexanes gradient)

Sources & evidence

ORD record
ord-f4ada0be6f464416977ddc3af8d45b44
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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