Hydrochloric Acid → HCID 24780655, compound

HRID 2241807Notes

Reaction equation

HRID 2241807 reaction equation
C[O:2][C:3]1[CH:19]=[CH:18][C:6]2[N:7]=[C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:16][CH3:17])=[N:14][CH:15]=3)[O:9][C:5]=2[CH:4]=1.Cl>C(Cl)Cl.C(OCC)C>[CH3:17][NH:16][C:13]1[N:14]=[CH:15][C:10]([C:8]2[O:9][C:5]3[CH:4]=[C:3]([OH:2])[CH:19]=[CH:18][C:6]=3[N:7]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 24780524HCID 24780524, compound

Product 1

HCID 24780655HCID 24780655, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

5-(6-Methoxy-1,3-benzoxazol-2-yl)-N-methylpyridin-2-amine (50 mg, 0.20 mmol) was dissolved in CH2Cl2 (10 mL) and made acidic with 2M HCl in diethylether. The solvent was removed in vacuo and hydrogen bromide (48% aq., 2 mL) was added. The reaction was run in a microwave reactor at 120° C. for 15 minutes. The mixture was then made basic with sodium bicarbonate and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by preparative HPLC, to give the title compound (11 mg) as a white solid. 1H NMR δ ppm 9.95 (br. s, 1H) 8.72 (d, 1H) 7.99 (dd, 1H) 7.46 (d, 1 H) 7.28 (d, 1 H) 7.03 (d, 1H) 6.79 (dd, 1H) 6.58 (d, 1H) 2.85 (d, 3H); MS m/z (M+H) 242, (M−H) 240.

Workup

  1. customThe solvent was removed in vacuo and hydrogen bromide (48% aq., 2 mL)
  2. additionwas added
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-96cacbefbefd48f6bb3c7bd3b954cf60
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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