Sodium Bicarbonate → HCID 67498868, compound

HRID 74265Notes

Reaction equation

HRID 74265 reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][CH2:4][NH:5][C:6]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][C:7]=1[NH2:8].Cl.[C:25](=N)(OC)[CH3:26].C(=O)([O-])O.[Na+]>CO>[O:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[C:10]1[CH:11]=[CH:12][C:6]2[N:5]([CH2:4][CH2:3][C:2]([F:1])([F:22])[F:23])[C:25]([CH3:26])=[N:8][C:7]=2[CH:9]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 674986742-(2-(3,3,3-Trifluoropropyl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 67498868HCID 67498868, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (5 mL) solution of 2-(2-(3,3,3-trifluoropropyl)aminoanilin-5-yl)benzoxazole (see Working Example 85-1) (300 mg, 0.93 mmol) was added methyl acetimidate hydrochloride (120 mg, 1.11 mmol), and this was heated to reflux for 3 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with chloroform. The organic layer obtained was dried over anhydrous sodium sulfate, after which it was filtered and concentrated to yield the title compound (250 mg, 93% yield) as white crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. extractionthis was extracted with chloroform
  4. customThe organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationafter which it was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0f8615389ce341508bbf451608ecf06d
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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