HCID 23533373, compound → HCID 9846456, compound

HRID 2414518Notes

Reaction equation

HRID 2414518 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[O:24][C:25]4[C:30]([C:31](=[O:33])[CH:32]=3)=[CH:29][CH:28]=[CH:27][C:26]=4[N:34]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]3)=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(OCC)(=O)C>[N:11]1([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[O:24][C:25]4[C:30]([C:31](=[O:33])[CH:32]=3)=[CH:29][CH:28]=[CH:27][C:26]=4[N:34]3[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]3)=[O:22])=[CH:16][CH:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 23533373HCID 23533373, compound

Product 1

HCID 9846456HCID 9846456, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

4-[4-({1-[8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromen-2-yl]-methanoyl}-amino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (Example 29) (160 mg, 0.3 mmol) was dissolved ethyl acetate (20 mL) and cooled to 0° C. HCl gas was bubbled in slowly for 2 minutes. A solid began to precipitate. Methanol (3-4 mL) was added to dissolve this solid and HCl gas was bubbled in for another 2 minutes. The mixture was concentrated under reduced pressure and triturated with ether and dried under vacuum to yield a tan solid (100 mg, 76%). LCMS/m/z=448.6.

Workup

  1. customHCl gas was bubbled in slowly for 2 minutes
  2. customto precipitate
  3. additionMethanol (3-4 mL) was added
  4. dissolutionto dissolve this solid and HCl gas
  5. customwas bubbled in for another 2 minutes
  6. concentrationThe mixture was concentrated under reduced pressure
  7. customtriturated with ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-6d992191cca7496397ab4a0b2ce26997
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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