Hydrochloric Acid → HCID 11955840, compound

HRID 600774

Reaction equation

HRID 600774 reaction equation
C([O:3][C:4]1[CH2:13][C:12]2[C:11]([NH:14][C:15]3[O:16][C:17]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:18][N:19]=3)=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH:5]=1)C.Cl.C([O-])(O)=O.[Na+]>O1CCCC1>[F:29][C:26]([F:27])([F:28])[C:23]1[CH:24]=[CH:25][C:20]([C:17]2[O:16][C:15]([NH:14][C:11]3[CH:10]=[CH:9][CH:8]=[C:7]4[C:12]=3[CH2:13][C:4](=[O:3])[CH2:5][CH2:6]4)=[N:19][CH:18]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67229299N-(7-ethoxy-5,8-dihydronaphthalen-1-yl)-5-[4-(trifluoromethyl)phenyl]-1,3-oxazol-2-amine

Product 1

HCID 11955840HCID 11955840, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of the product of Example 1H (150 mg, 0.375 mmol) in tetrahydrofuran (2.3 mL) was treated with 2N HCl (0.76 mL, 1.52 mmol), and the mixture was heated at 40° C. for 1 hour. After cooling to room temperature, the solution was brought to pH 8 with saturated NaHCO3 solution, and extracted with ethyl acetate. The organic extracts were washed with H2O, dried over Na2SO4, filtered and evaporated in vacuo to the title compound as a brown residue (140 mg, 100%). 1H NMR (DMSO-d6) δ 9.56 (s, 1H), 7.78 (m, 4H), 7.67 (d, 1H, J=7.8 Hz), 7.62 (s, 1H), 7.22 (t, 1H, J=7.8 Hz), 7.06 (d, 1H, J=7.4 Hz), 3.58 (s, 2H), 3.36 (m, 2H), 3.06 (t, 2H, J=6.8 Hz); MS (ESI+) m/z 373 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo to the title compound as a brown residue (140 mg, 100%)

Sources & evidence

ORD record
ord-881d0d0f502e4173bb6141fbfdb8aff9
Source dataset
uspto-grants-2011_03
Patent number
US07902236B2

Linked notes

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