Potassium Carbonate → 4-[(6-Chloronaphthalen-2-yl)sulfonyl]-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-2-[[N-(tetrahydropyran-2-yloxy)]carbamoyl]piperazine

HRID 352959Notes

Reaction equation

HRID 352959 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[S:24][C:25]4[CH2:26][NH:27][CH:28]([CH3:32])[CH2:29][C:30]=4[N:31]=3)=[O:22])[CH:17]([C:33](O)=[O:34])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[O:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]1[O:42][NH2:43].O.ON1C2C=CC=CC=2N=N1.Cl.CN(CCCN=C=NCC)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[S:24][C:25]4[CH2:26][NH:27][CH:28]([CH3:32])[CH2:29][C:30]=4[N:31]=3)=[O:22])[CH:17]([C:33](=[O:34])[NH:43][O:42][CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][O:36]3)[CH2:16]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 227103534-[(6-Chloronaphthalen-2-yl)sulfonyl]-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine-2-carboxylic Acid

Product 1

HCID 227106624-[(6-Chloronaphthalen-2-yl)sulfonyl]-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-2-[[N-(tetrahydropyran-2-yloxy)]carbamoyl]piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (20 ml), 4-[(6-chloronaphthalen-2-yl)sulfonyl]-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine-2-carboxylic acid (141 mg), 2-tetrahydropyranyloxyamine (180 mg), 1-hydroxybenzotriazole monohydrate (11 mg), 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (145 mg) and potassium carbonate (129 mg) were dissolved, followed by stirring overnight at room temperature. The reaction mixture was concentrated under reduced pressure. Dichloromethane was added to the residue, followed by washing with water. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (Φ0.7×25.0 cm, dichloromethane:methanol=100:3), whereby the title compound (308 mg) was obtained as a colorless foam.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionDichloromethane was added to the residue
  3. washby washing with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column (Φ0.7×25.0 cm, dichloromethane:methanol=100:3), whereby the title compound (308 mg)
  7. customwas obtained as a colorless foam

Sources & evidence

ORD record
ord-3ffb8913ae894288842cf03074abbf4f
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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