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Sodium Bicarbonate → 6-amino-4-[2-[4-(thieno[3,2-c]pyridin-4-yl)-1-piperazinyl]ethyl]-2(1H)-quinolone hydrochloride

HRID 619121
Notes
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Reaction equation

HRID 619121 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7]=[C:6]2[CH2:14][CH2:15][Cl:16].[N:17]1([C:23]2[C:28]3[CH:29]=[CH:30][S:31][C:27]=3[CH:26]=[CH:25][N:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[ClH:16].[NH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7]=[C:6]2[CH2:14][CH2:15][N:20]1[CH2:21][CH2:22][N:17]([C:23]2[C:28]3[CH:29]=[CH:30][S:31][C:27]=3[CH:26]=[CH:25][N:24]=2)[CH2:18][CH2:19]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 109660274-(Piperazin-1-yl)thieno[3,2-c]pyridineHCID 218460266-amino-4-(2-chloroethyl)-2(1H)-quinolone hydrochloride

Product 1

HCID 218460546-amino-4-[2-[4-(thieno[3,2-c]pyridin-4-yl)-1-piperazinyl]ethyl]-2(1H)-quinolone hydrochloride

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.35 g (1.35 mmol) of 6-amino-4-(2-chloroethyl)-2(1H)-quinolone hydrochloride, 0.33 g (1.5 mmol) of 4-(1-piperazinyl)thieno[3,2-c]pyridine and 0.17 g (2 mmol) of sodium bicarbonate in 10 ml of dimethylformamide is heated to 60° C. for 24 hours. After cooling to room temperature, the reaction medium is diluted in 50 ml of water and the crude product is extracted with chloroform. The organic phase is dried over sodium sulpbate and concentrated. The crude product is purified by flash chromatography on silica, eluting first with a methanol/ethyl acetate (6.5:93.5) mixture containing traces of triethylamine and then with a methanol/dichloromethane (6.5:93.5) mixture comprising traces of aqueous ammonia.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe crude product is extracted with chloroform
  3. dry with materialThe organic phase is dried over sodium sulpbate
  4. concentrationconcentrated
  5. customThe crude product is purified by flash chromatography on silica
  6. washeluting first with a methanol/ethyl acetate (6.5:93.5) mixture
  7. additioncontaining traces of triethylamine

Sources & evidence

ORD record
ord-1ced206f81b74818b59db6b2120e60f8
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05958924

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes