Piperidine → HCID 57637311, compound

HRID 2078743Notes

Reaction equation

HRID 2078743 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH2:16]OS(C)(=O)=O)[S:15][C:11]=2[C:10]([I:22])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>ClCCl>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH2:16][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[S:15][C:11]=2[C:10]([I:22])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 57637319HCID 57637319, compound2×

Product 1

HCID 57637311HCID 57637311, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-iodo-5-methanesulfonyloxymethyl-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [210 mg, 0.46 mmol, Intermediate (81)] in dichloromethane (3 mL) were added triethylamine (70 μL, 0.55 mmol), and piperidine (55 μL, 0.55 mmol). The mixture was stirred at room temperature for 1 hour. The solvent was removed and the residue was chromatographed through silica gel (dichloromethane/ethyl acetate, 95/05 as eluant) to produce 3-iodo-5-piperidin-1-ylmethyl-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [110 mg, 53%, Intermediate (82)] as a white foam. LC/MS: 448.0 (M+H), RT=2.55 minutes.

Workup

  1. customThe solvent was removed
  2. customthe residue was chromatographed through silica gel (dichloromethane/ethyl acetate, 95/05 as eluant)

Sources & evidence

ORD record
ord-e02e6956bedb49beb732a9c7e664857e
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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