tert-Butyl piperazine-1-carboxylate → 1-(tert-Butoxycarbonyl)-4-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine

HRID 352873Notes

Reaction equation

HRID 352873 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+].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O.C(Cl)Cl>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:11]([C:9]2[S:8][C:5]3[CH2:6][NH:7][CH:2]([CH3:1])[CH2:3][C:4]=3[N:10]=2)=[O:13])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

8

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23674323Lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

Product 1

HCID 227103621-(tert-Butoxycarbonyl)-4-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate (293 mg) in N,N-dimethylformamide (10 ml) were added 1-(tert-butoxycarbonyl)piperazine (294 mg), 1-hydroxybenzotriazole monohydrate (214 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (303 mg) at room temperature. After stirring for 38 hours, methylene chloride (20 ml) and water (200 ml) were added to the reaction mixture to separate it into layers. The water layer thus obtained was extracted with methylene chloride (3×10 ml). The organic layers were combined, washed with a saturated aqueous solution (100 ml.) of sodium bicarbonate, 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 (methylene chloride:acetone=2:1), whereby the title compound (300 mg) was obtained as a pale yellow viscous substance.

Workup

  1. customto separate it into layers
  2. customThe water layer thus obtained
  3. extractionwas extracted with methylene chloride (3×10 ml)
  4. washwashed with a saturated aqueous solution (100 ml.) of sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column (methylene chloride:acetone=2:1), whereby the title compound (300 mg)
  9. customwas obtained as a pale yellow viscous substance

Sources & evidence

ORD record
ord-972b48834fbd4c18bc7818c52705bf63
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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