Picolinic acid → HCID 18689947, compound

HRID 1871942Notes

Reaction equation

HRID 1871942 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][NH2:6])[CH2:3][NH2:4].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([OH:16])=O.[OH2:17].ON1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=N1.Cl.CN(C)CCCN=C=NCC.CCN(C(C)C)C(C)C>CN(C=O)C>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=1[C:27]([NH:4][CH2:3][C:2]([CH3:7])([CH3:1])[CH2:5][NH:6][C:14](=[O:16])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=1)=[O:17]

Participants

7

Reactant 5

HCID 1018Picolinic acidHCID 81531DiisopropylethylamineHCID 817702,2-Dimethyl-1,3-propanediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 18689947HCID 18689947, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,2-dimethyl-1,3-propanediamine (5.00 g, 48.9 mmol) in DMF (500 mL) was treated with picolinic acid (12.6 g, 0.10 mol), 1-hydroxybenzotriazole hydrate (13.9 g, 0.10 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (19.7 g, 0.10 mol) and iPr2NEt (17.9 mL, 0.10 mol) at room temperature. After 18 h, the reaction mixture was evaporated under vacuum and the residue purified by flash chromatography (75% EtOAc/hexanes, silica gel) to give 13.95 g (91%) the above named product as a clear solid. A fraction of this product (5.63 g) was recrystallized from ethyl acetate/hexane by slow evaporation to give 3.92 g of pure product as white needles. MS (ES+) m/e 313 [M+H+ ].

Workup

  1. customthe reaction mixture was evaporated under vacuum
  2. customthe residue purified by flash chromatography (75% EtOAc/hexanes, silica gel)
  3. customto give 13.95 g (91%) the above named product as a clear solid
  4. customA fraction of this product (5.63 g) was recrystallized from ethyl acetate/hexane by slow evaporation

Sources & evidence

ORD record
ord-9b10a3d911954001a1be8b9cb47a88dd
Source dataset
uspto-grants-2000_08
Patent number
US06107309

Reaction notes

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