Triethylamine → HCID 57523482, compound

HRID 1695250Notes

Reaction equation

HRID 1695250 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([NH:13][C:14](=[O:21])[CH:15]([CH3:20])[CH2:16][CH2:17][CH2:18]Br)=[CH:11][C:10]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[N:37]1([C:44](=[O:46])[CH3:45])[CH2:43][CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:12]([NH:13][C:14](=[O:21])[CH:15]([CH3:20])[CH2:16][CH2:17][CH2:18][N:40]2[CH2:41][CH2:42][CH2:43][N:37]([C:44](=[O:46])[CH3:45])[CH2:38][CH2:39]2)=[CH:11][C:10]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 4186202N-AcetylhomopiperazineHCID 57500980HCID 57500980, compound

Product 1

HCID 57523482HCID 57523482, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(5-Bromo-2-methyl-pentanoylamino)-3-(4-methoxy-phenyl)-pyrazole-1-carboxylic acid tert-butyl ester (280.0 mg, 0.6 mmol, 1.0 eq) was dissolved in DCM (3 mL). Triethylamine (80 μL, 0.6 mmol, 1.0 eq) and 1-[1,4]-diazepan-1-yl-ethanone (158 μL, 170.0 mg, 1.2 mmol, 2.0 eq) were added and the mixture was stirred at room temperature for 24 hours, then at 50° C. for 16 hours. NaHCO3 saturated solution was added and the organic layer separated and collected. Evaporation of the solvent gave a crude product purified using SiO2 column (elution DCM, DCM:MeOH 99:1 to 96:4) obtaining the title product (181.3 mg, yield 54%).

Workup

  1. waitat 50° C. for 16 hours
  2. customthe organic layer separated
  3. customcollected
  4. customEvaporation of the solvent
  5. customgave a crude product
  6. custompurified
  7. washSiO2 column (elution DCM, DCM:MeOH 99:1 to 96:4)

Sources & evidence

ORD record
ord-8265445f13914c9784c58538b5853917
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

Loading…