Hydrochloric Acid → HCID 72360026, compound

HRID 1881658Notes

Reaction equation

HRID 1881658 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([NH:15][N:16]=[C:17]([C:19]2[C:23]([OH:24])=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=3)[S:21][CH:20]=2)[CH3:18])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:50][N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1.Cl>CN1CCCC1=O>[C:31]([C:28]1[CH:27]=[CH:26][C:25]([C:22]2[S:21][CH:20]=[C:19]([C:17](=[N:16][NH:15][C:13](=[O:14])[C:11]3[CH:10]=[CH:9][C:5]([C:6]([N:54]4[CH2:55][CH2:56][N:51]([CH3:50])[CH2:52][CH2:53]4)=[O:7])=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=3)[CH3:18])[C:23]=2[OH:24])=[CH:30][CH:29]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 62365Isobutyl chloroformateHCID 72360107HCID 72360107, compound

Product 1

HCID 72360026HCID 72360026, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a N-methyl-2-pyrrolidinone (1.0 mL) solution of 2-nitro-4-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]-ethylidene}hydrazino)carbonyl]benzoic acid (50 mg, 0.10 mmol, see the synthetic example 47) and triethylamine (16 μL, 0.11 mmol) was added isobutyl chloroformate (26 μL, 0.20 mmol) at 0° C. The reaction mixture was stirred for 2 hours at this temperature, and then N-methyl piperazine (45 μL, 0.40 mmol) was added. After stirring for 1 hour at room temperature, the reaction mixture was acidified with 1M aqueous HCl solution (1.0 mL) and concentrated under the reduced pressure. To the residue was added water, then the precipitate was collected by filtration, washed with water, isopropanol and methanol, then dried by means of a vacuum pump to give the desired product as a pale yellow solid (yield 10%).

Workup

  1. stirringAfter stirring for 1 hour at room temperature
  2. concentrationconcentrated under the reduced pressure
  3. additionTo the residue was added water
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water, isopropanol and methanol
  6. customdried by means of a vacuum pump

Sources & evidence

ORD record
ord-9a82d3138f7a4e70896785b451799d7c
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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