1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 4-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-[(N-methyl)carbamoyl]-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine Hydrochloride

HRID 352945Notes

Reaction equation

HRID 352945 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][C:5]2[S:8][C:9]([C:11]([O-:13])=O)=[N:10][C:4]=2[CH2:3]1.[Li+].FC(F)(F)C(O)=O.[Cl:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[CH:29]=[C:28]([S:33]([N:36]1[CH2:41][CH2:40][NH:39][CH:38]([C:42](=[O:45])[NH:43][CH3:44])[CH2:37]1)(=[O:35])=[O:34])[CH:27]=[CH:26]2.O.ON1C2C=CC=CC=2N=N1.Cl.CN(CCCN=C=NCC)C>CN(C)C=O.Cl>[ClH:22].[Cl:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[CH:29]=[C:28]([S:33]([N:36]1[CH2:41][CH2:40][N:39]([C:11]([C:9]3[S:8][C:5]4[CH2:6][NH:7][CH:2]([CH3:1])[CH2:3][C:4]=4[N:10]=3)=[O:13])[CH:38]([C:42](=[O:45])[NH:43][CH3:44])[CH2:37]1)(=[O:34])=[O:35])[CH:27]=[CH:26]2

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 227095024-[(6-chloronaphthalen-2-yl)sulfonyl]-2-[(N-methyl)carbamoyl]piperazine trifluoroacetateHCID 23674323Lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

Product 1

HCID 227101714-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-[(N-methyl)carbamoyl]-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine Hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (100 ml), lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-carboxylate (616 mg), 4-[(6-chloronaphthalen-2-yl)sulfonyl]-2-[(N-methyl)carbamoyl]piperazine trifluoroacetate (1.12 g), 1-hydroxybenzotriazole monohydrate (36 mg) and 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (579 mg) were dissolved and the resulting solution was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. Dichloromethane was then added to the residue, followed by washing with water. The organic layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column [Φ3.0×(1.5+8) cm, ethyl acetate:methanol=100:4], whereby a colorless foam was obtained. The resulting foam was dissolved in 1N HCl (20 ml), followed by concentration under reduced pressure, whereby the title compound (845 mg) was obtained as a pale yellow foam.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionDichloromethane was then added to the residue
  3. washby washing with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column [Φ3.0×(1.5+8) cm, ethyl acetate:methanol=100:4], whereby a colorless foam
  8. customwas obtained
  9. concentrationfollowed by concentration under reduced pressure, whereby the title compound (845 mg)
  10. customwas obtained as a pale yellow foam

Sources & evidence

ORD record
ord-0caada7cd18545058805d29a005ab2b5
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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