Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 7-[({5-[1-Hydroxy-1-(trifluoromethyl)propyl]-1,3,4-oxadiazol-2-yl}amino)methyl]-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

HRID 1988218Notes

Reaction equation

HRID 1988218 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=O)=[CH:14][CH:15]=3)[O:10][C:9](=[O:19])[CH:8]=2)[N:6]=1.[NH2:20][C:21]1[O:25][C:24]([C:26]([OH:33])([CH2:31][CH3:32])[C:27]([F:30])([F:29])[F:28])=[N:23][N:22]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[OH:33][C:26]([C:24]1[O:25][C:21]([NH:20][CH2:17][C:13]2[CH:12]=[C:11]3[C:16]([C:7]([C:5]4[N:6]=[C:2]([CH3:1])[S:3][CH:4]=4)=[CH:8][C:9](=[O:19])[O:10]3)=[CH:15][CH:14]=2)=[N:22][N:23]=1)([C:27]([F:29])([F:28])[F:30])[CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 4311764Sodium borohydrideHCID 469421982-(5-Amino-1,3,4-oxadiazol-2-yl)-1,1,1-trifluorobutan-2-olHCID 577292574-(2-Methyl-1,3-thiazol-4-yl)-2-oxo-2H-chromene-7-carbaldehyde

Product 1

HCID 118550917-[({5-[1-Hydroxy-1-(trifluoromethyl)propyl]-1,3,4-oxadiazol-2-yl}amino)methyl]-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(2-methyl-1,3-thiazol-4-yl)-2-oxo-2H-chromene-7-carbaldehyde (0.200 g, 0.74 mmol) and 2-(5-amino-1,3,4-oxadiazol-2-yl)-1,1,1-trifluorobutan-2-ol (0.202 g, 0.96 mmol) in toluene (2 ml) was added PPTS (0.019 g, 0.07 mmol). The reaction mixture was heated under reflux with a Dean-Stark trap for 6 h. After evaporation, the residue was diluted in EtOH (2 ml), cooled to 0° C. and sodium borohydride (28 mg, 0.74 mmol) was added. After 15 min, the reaction was quenched with a saturated solution of NH4Cl, extract with EtOAc then washed with water and brine. The solvent was evaporated and the residue chromatographed on silica gel (chloroform-ethanol, 95:5) to give the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.27 (d, 1H), 8.09 (s, 1H), 7.45 (m, 3H), 6.66 (s, 1H), 6.08 (s, 1H), 4.7 (d, 2H), 2.83 (s, 3H), 2.22 (m, 1H), 2.10 (m, 1H), 0.98 (m, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux with a Dean-Stark trap for 6 h
  3. customAfter evaporation
  4. additionthe residue was diluted in EtOH (2 ml)
  5. customthe reaction was quenched with a saturated solution of NH4Cl
  6. extractionextract with EtOAc
  7. washthen washed with water and brine
  8. customThe solvent was evaporated
  9. customthe residue chromatographed on silica gel (chloroform-ethanol, 95:5)

Sources & evidence

ORD record
ord-43a70c5d1db24814a20eabb552653624
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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