Hydrochloric Acid → HCID 67188117, compound

HRID 1695252Notes

Reaction equation

HRID 1695252 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH:5]([CH3:9])[C:6]([OH:8])=O.C(Cl)Cl.[C:13]([O:17][C:18]([N:20]1[C:24]([NH2:25])=[CH:23][C:22]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[N:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C.Cl>>[C:13]([O:17][C:18]([N:20]1[C:24]([NH:25][C:6](=[O:8])[CH:5]([CH3:9])[CH2:4][CH2:3][CH2:2][Br:1])=[CH:23][C:22]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)=[N:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 8471TriethylamineHCID 21251747HCID 21251747, compound2×HCID 67186522HCID 67186522, compound

Product 1

HCID 67188117HCID 67188117, compoundYield 97%

Procedure

To a solution of 5-bromo-2-methyl-pentanoic acid (1.79 g, 9.2 mmol, 1 eq) in anhydrous DCM (8 mL) oxalyl chloride (1.0 mL, 12.0 mmol, 1.3 eq) was added dropwise and the mixture was stirred at room temperature for 16 hours. After evaporation of the solvent and the excess oxalyl chloride, the residue was dissolved in anhydrous DCM (8 mL) and a solution of 5-amino-3-(4-chloro-phenyl)-pyrazole-1-carboxylic acid tert-butyl ester (2.7 g, 9.2 mmol, 1.0 eq) and triethylamine (1.7 mL, 12 mmol, 1.3 eq) was added dropwise at 0° C. The mixture was allowed to reach room temperature and stirred at room temperature for 24 hours, after which another 0.5 eq of activated 5-bromo-2-methyl-pentanoic acid was added. HCl 1M was added; the crude was extracted with DCM and purified through SiO2 column (eluent DCM) to give 3.3 g (yield 97%) of the title product.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe excess oxalyl chloride, the residue was dissolved in anhydrous DCM (8 mL)
  3. customto reach room temperature
  4. stirringstirred at room temperature for 24 hours
  5. extractionthe crude was extracted with DCM
  6. custompurified through SiO2 column (eluent DCM)

Sources & evidence

ORD record
ord-5f829ba6717e4fbdbb4cd761b0772500
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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