1-Pyrrolidineethanamine → 5-Bromo-pyridine-2-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide

HRID 1662819Notes

Reaction equation

HRID 1662819 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[N:29]1([CH2:34][CH2:35][NH2:36])[CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl>[N:29]1([CH2:34][CH2:35][NH:36][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[O:10])[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 6085445-Bromopyridine-2-carboxylic acid

Product 1

HCID 587487285-Bromo-pyridine-2-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-pyridine-2-carboxylic acid (0.81 g, 4 mmol) was combined with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) (0.85 g, 4.8 mmol) and diluted with DCM (20 mL). This was immediately treated with 4-methyl morpholine (0.81 g, 8 mmol) and allowed to stir at ambient temperature for 1 h. 2-Pyrrolidin-1-yl-ethylamine (0.46 g, 4 mmol) was then added in one portion. Stirring was continued overnight. Reaction solvents were removed and residue was taken up in ethyl acetate and washed once with water. Aqueous phase was back extracted once with fresh ethyl acetate. Organic phases were combined, washed once with brine and dried over sodium sulfate. Filtration followed by rotary evaporation provided product as yellow oil which solidified upon standing. Yellowish solids (0.5 g, 42%)

Workup

  1. stirringStirring
  2. waitwas continued overnight
  3. customReaction solvents
  4. customwere removed
  5. washwashed once with water
  6. extractionAqueous phase was back extracted once with fresh ethyl acetate
  7. washwashed once with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationFiltration
  10. customfollowed by rotary evaporation
  11. customprovided product as yellow oil which

Sources & evidence

ORD record
ord-ef722978a0304ab0a35ae732a39023e0
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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