Dimethylamine → HCID 178484499, compound

HRID 908473Notes

Reaction equation

HRID 908473 reaction equation
[N:1]1(C(N2C=CN=C2)=O)[CH:5]=CN=[CH:2]1.[Br:13][C:14]1[C:15]([C:19]([OH:21])=O)=[N:16][NH:17][CH:18]=1.CNC>C(Cl)Cl.C1COCC1>[Br:13][C:14]1[C:15]([C:19]([N:1]([CH3:5])[CH3:2])=[O:21])=[N:16][NH:17][CH:18]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178524944HCID 178524944, compound

Product 1

HCID 178484499HCID 178484499, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

di(imidazol-1-yl)methanone (1910 mg) was added portionwise to a suspension of 4-bromo-1H-pyrazole-3-carboxylic acid (900 mg) in DCM (18 ml).After 2 hours dimethylamine 2M in THF (9.42 ml) was added portionwise and the mixture was stirred overnight. The reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (5 microns silica, 30 mm diameter, 150 mm length) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions were evaporated to dryness to afford 4-bromo-N,N-dimethyl-1H-pyrazole-3-carboxamide (471 mg) as a solid. NMR Spectrum: (DMSOd6): 2.95 (s, 3H), 2.98 (s, 3H), 7.99 (s, 1H); Mass spectrum: M+H+ 220.

Workup

  1. additionwas added portionwise
  2. customThe reaction mixture was purified by preparative HPLC
  3. customThe fractions were evaporated to dryness

Sources & evidence

ORD record
ord-0629fbcd1a2f49dd95899131f6461465
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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