Sodium ethoxide → HCID 86636078, compound

HRID 1642425Notes

Reaction equation

HRID 1642425 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:21][CH:20]=[CH:19][N:5]2[C:6](=[O:18])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[CH2:22]1[CH2:24][CH:23]1[CH2:25][O:26][C:27]1C=CC=CC=1C=O.[O-]CC.[Na+]>C(O)C>[CH2:22]1[CH2:24][CH:23]1[CH2:25][O:26]/[CH:27]=[CH:1]/[C:2]1[N:3]=[C:4]2[S:21][CH:20]=[CH:19][N:5]2[C:6](=[O:18])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 1495552954280-77-2HCID 667528027-Methyl-6-[4-(trifluoromethyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 86636078HCID 86636078, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Intermediate 5 (400 mg, 1.289 mmol), (2-cyclopropylmethoxy)benzaldehyde (356 mg, 2.025 mmol) and sodium ethoxide (183 mg, 2.108 mmol) in ethanol (20 ml) was refluxed for 15 h. The reaction mixture was concentrated, the residue extracted with ethyl acetate, washed with water and brine to afford crude solid which was purified by column chromatography to afford 241 mg of the desired compound as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.12-0.20 (m, 2H), 0.27-0.32 (m, 2H), 0.78-0.83 (m, 1H), 3.74 (d, J=6.9 Hz, 2H), 6.90-6.97 (m, 2H), 7.18-7.26 (m, 2H), 7.39 (d, J=6.9 Hz, 1H), 7.52 (d, J=4.8 Hz, 1H), 7.58 (d, J=7.8 Hz, 2H), 7.80 (d, J=7.5 Hz, 2H), 7.91-7.97 (m, 1H), 8.00 (d, J=4.5 Hz, 1H); ESI-MS (m/z) 469.22 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue extracted with ethyl acetate
  3. washwashed with water and brine
  4. customto afford crude solid which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-91a276a042a3428283097d0f70320184
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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