1,2-Dichloroethane → HCID 178452121, compound

HRID 20301

Reaction equation

HRID 20301 reaction equation
[N+:1]([C:4]1[C:5]([C:9]([OH:11])=O)=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([NH:12][C:9]([C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][NH:7][N:6]=2)=[O:11])[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 12682914-Amino-1-Boc-piperidineHCID 178524956HCID 178524956, compound

Product 1

HCID 178452121HCID 178452121, compoundYield 241.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitropyrazole-3-carboxylic acid (7.3 g; 15.9 mmol) was added to a stirred solution of 4-amino-1-Boc-piperidine (10.2 mg; 51 mmol), EDC (10.7 g; 55.8 mmol), and HOAt (55.8 g; 19.1 mmol) in DMF (100 ml), and then stirred at room temperature overnight. The solvent was removed by evaporation under reduced pressure and the residue triturated with water (250 ml). The resultant cream solid was collected by filtration, washed with water then dried under vacuum to give 13.05 g of 4-[(4-nitro-1H-pyrazole-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (LC/MS: Rt 2.50, [M+H]+ 340).

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe residue triturated with water (250 ml)
  3. filtrationThe resultant cream solid was collected by filtration
  4. washwashed with water
  5. customthen dried under vacuum

Sources & evidence

ORD record
ord-8b338840c5a64f9791112d830be7d25a
Source dataset
uspto-grants-2010_06
Patent number
US07745638B2

Linked notes

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