Acetic Acid Mixture with Hydrobromic Acid → HCID 20703610, compound

HRID 429309Notes

Reaction equation

HRID 429309 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[NH:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[CH2:13][C@H:12]1[C@@H:30]([NH:32][C:33]1[N:38]=[C:37]([N:39]2[C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=3[N:41]=[CH:40]2)[CH:36]=[CH:35][N:34]=1)[CH3:31])=O)C1C=CC=CC=1.Br.CC(O)=O>C(Cl)Cl.O>[C:19]1([NH:18][C:17]([N:14]2[CH2:15][CH2:16][NH:11][C@H:12]([C@@H:30]([NH:32][C:33]3[N:38]=[C:37]([N:39]4[C:43]5[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=5[N:41]=[CH:40]4)[CH:36]=[CH:35][N:34]=3)[CH3:31])[CH2:13]2)=[O:29])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 70212198HCID 70212198, compound

Product 1

HCID 20703610HCID 20703610, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S,S)-2-[1-(1-(benzyloxycarbonyl)-4-(N-naphth-1-yl-carbamoyl)piperazin-2-yl)ethylamino]-4-[benzi midazol-1-yl]pyrimidine (24 mg) dissolved in 2 mL of CH2Cl2 and cooled to 0° C. was added 1 mL of 30% HBr/AcOH. The reaction mixture was stirred for 10 minutes at 0° C., then stirred for an additional 2 hours while warming to room temperature. The mixture was diluted with 5 mL of water and extracted with 2×5 mL of CH2Cl2. The aqueous layer was basified to pH 11 using 5N NaOH and extracted with 5×5 mL of ethyl acetate while maintaining a pH of 11. The combined organic phases were washed with 10 nL of brine, dried with Na2SO4, and concentrated to provide 9.6 mg the title compound. Mass spectrum (ESI) 493.3 (M+1).

Workup

  1. stirringstirred for an additional 2 hours
  2. temperaturewhile warming to room temperature
  3. extractionextracted with 2×5 mL of CH2Cl2
  4. extractionextracted with 5×5 mL of ethyl acetate
  5. temperaturewhile maintaining a pH of 11
  6. washThe combined organic phases were washed with 10 nL of brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2642b97c737b4aec86f8a0fff8710f36
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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