6-[4-(2-tert-Butoxycarbonylamino-4-methylthiazole-5-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone → 6-[4-(2-amino-4-methylthiazole-5-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone

HRID 704635

Reaction equation

HRID 704635 reaction equation
C(OC([NH:8][C:9]1[S:10][C:11]([C:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]4)[CH2:19][CH2:18]2)=[O:16])=[C:12]([CH3:14])[N:13]=1)=O)(C)(C)C>C(O)=O>[NH2:8][C:9]1[S:10][C:11]([C:15]([N:17]2[CH2:18][CH2:19][N:20]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]4)[CH2:21][CH2:22]2)=[O:16])=[C:12]([CH3:14])[N:13]=1

Participants

3

Reactant 1

HCID 200728916-[4-(2-tert-Butoxycarbonylamino-4-methylthiazole-5-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 200727936-[4-(2-amino-4-methylthiazole-5-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinoneYield 95.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

6-[4-(2-tert-Butoxycarbonylamino-4-methylthiazole-5-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone (1.2 g) was dissolved in formic acid (25 ml) and the solution was stirred for 4 hours at ambient temperature. After the solvent was removed, ethyl acetate (10 ml) and water (10 ml) was added to the residue and the mixture was adjusted to pH 4.5 with 10% aqueous solution of potassium carbonate. The resulting precipitate was collected and recrystallized from methanol-water to give 6-[4-(2-amino-4-methylthiazole-5-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone (0.9 g).

Workup

  1. customAfter the solvent was removed
  2. additionethyl acetate (10 ml) and water (10 ml) was added to the residue
  3. customThe resulting precipitate was collected
  4. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-5682d432bcc64531b954917cebff8033
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Linked notes

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