Toluene → HCID 22993994, compound

HRID 1167833Notes

Reaction equation

HRID 1167833 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([C:11]2[N:15]=[C:14]([C:16]3[S:20][C:19]([NH:21][C:22]4[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=4)=[N:18][C:17]=3[NH2:34])[O:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>O1CCOCC1>[NH2:34][C:17]1[N:18]=[C:19]([NH:21][C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=2)[S:20][C:16]=1[C:14]1[O:13][N:12]=[C:11]([C:7]2[CH:6]=[C:5]([OH:4])[CH:10]=[CH:9][CH:8]=2)[N:15]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 53955924HCID 53955924, compound

Product 1

HCID 22993994HCID 22993994, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 200 mg (0.412 mmol) of 5-[3-(3-methoxymethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-N2-(3,4,5-trimethoxy-phenyl)-thiazole-2,4-diamine (prepared in Example B(4)) in 8 mL of 50% aqueous dioxane was added trifluoroacetic acid (8 mL) with water bath cooling at 15° C. After 2 hours at room temperature, toluene was added, and the solution was concentrated in vacuo with the water bath at 22° C. With five milliliters of solvent left, the solution was poured into cold aqueous sodium bicarbonate. This solution was extracted with two portions of dichloromethane, which was subsequently washed with brine and dried over sodium sulfate. Radial silica chromatography eluting with 5-10% methanol/dichloromethane gave 3-{5-[4-amino-2-(3,4,5-trimethoxy-phenylamino)-thiazol-5-yl]-[1,2,4]oxadiazol-3-yl}-phenol (60 mg) as a pale-yellow solid.

Workup

  1. concentrationthe solution was concentrated in vacuo with the water bath at 22° C
  2. waitWith five milliliters of solvent left
  3. additionthe solution was poured into cold aqueous sodium bicarbonate
  4. extractionThis solution was extracted with two portions of dichloromethane, which
  5. washwas subsequently washed with brine
  6. dry with materialdried over sodium sulfate
  7. washRadial silica chromatography eluting with 5-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-922804854054402b8c8d1e40c81246d0
Source dataset
uspto-grants-2003_09
Patent number
US06620828B2

Reaction notes

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