Methanol → HCID 67497701, compound

HRID 74268

Reaction equation

HRID 74268 reaction equation
CO.[CH:3]1([NH:13][C:14]2[CH:20]=[CH:19][C:18]([C:21]3[O:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[N:25]=3)=[CH:17][C:15]=2[NH2:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.Cl.[C:31](=N)(OC)[CH3:32]>O>[O:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[C:18]1[CH:19]=[CH:20][C:14]2[N:13]([CH:3]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH2:6][CH2:5][CH2:4]3)[C:31]([CH3:32])=[N:16][C:15]=2[CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 674979522-(2-(1,2,3,4-Tetrahydronaphthalen-1-yl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 67497701HCID 67497701, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methanol (5 mL) solution of 2-(2-(1,2,3,4-tetrahydronaphthalen-1-yl)aminoanilin-5-yl)benzoxazole (see Working Example 87-1) (0.30 g, 0.8 mmol) was added methyl acetimidate hydrochloride (0.10 g, 0.9 mmol), and this was heated to reflux for 3 hours. After the reaction solution was cooled, water was added, and this was extracted with chloroform. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (0.15 g, 47% yield) as a colorless amorphous mass.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. temperatureAfter the reaction solution was cooled
  4. extractionthis was extracted with chloroform
  5. customAfter the organic layer obtained
  6. dry with materialwas dried over anhydrous sodium sulfate, it
  7. filtrationwas filtered
  8. concentrationconcentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7c8af375083148a3996f5290d4cb4ece
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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