Hydrochloric Acid → HCID 86755974, compound

HRID 369895Notes

Reaction equation

HRID 369895 reaction equation
[CH:1]([C:4]1[CH:23]=[C:22]([C:24](=[O:30])[CH:25]=[CH:26][C:27](O)=[O:28])[CH:21]=[CH:20][C:5]=1[O:6][CH2:7][C:8]([NH:10][C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)=[O:9])([CH3:3])[CH3:2].[CH3:31][N:32]1[CH2:37][CH2:36][N:35]([CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:34][CH2:33]1.P(C#N)(OCC)(OCC)=O.[ClH:54]>CN(C)C=O.O.C(N(CC)CC)C>[ClH:54].[ClH:54].[CH:1]([C:4]1[CH:23]=[C:22]([C:24](=[O:30])[CH:25]=[CH:26][C:27]([N:41]2[CH2:40][CH2:39][CH:38]([N:35]3[CH2:34][CH2:33][N:32]([CH3:31])[CH2:37][CH2:36]3)[CH2:43][CH2:42]2)=[O:28])[CH:21]=[CH:20][C:5]=1[O:6][CH2:7][C:8]([NH:10][C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)=[O:9])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 76257Diethyl cyanophosphonateHCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 54214798HCID 54214798, compound

Product 1

HCID 86755974HCID 86755974, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-[2-isopropyl-4-(3-carboxyacryloyl)phenoxymethylcarbonylamino]benzothiazole (0.97 g) in dimethylformamide (10 ml) are added dropwise 4-(4-methyl-1-piperazinyl)piperidine (0.65 g) and diethyl cyanophosphate (0.6 ml) at room temperature. To the mixture is added triethylamine (0.5 ml), and the mixture is stirred at room temperature for 10 minutes. To the mixture is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=100:1→10:1). The compound thus obtained is converted into a hydrochloride thereof in ethanol by a conventional method, and recrystallized from ethanol-diethyl ether to give 2-{2-isopropyl-4-[3-[4-(4-methyl-1-piperazinyl)-1-piperidinylcarbonyl]acryloyl]phenoxymethylcarbonylamino}benzothiazole dihydrochloride (0.45 g).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=100:1→10:1)
  6. customThe compound thus obtained
  7. customin ethanol by a conventional method, and recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-81782401485c464a84c68d66f4746be0
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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