Diisopropylethylamine → 4-Amino-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)picolinamide

HRID 2407812Notes

Reaction equation

HRID 2407812 reaction equation
Cl.Cl.Cl.[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][NH2:23])[CH2:18][CH2:17]2)=[CH:13][N:14]=1.Cl.C(N=C=NCCCN(C)C)C.[NH2:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([C:43](O)=[O:44])[CH:38]=1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CC(N(C)C)=O.C(OCC)(=O)C>[NH2:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([C:43]([NH:23][CH2:22][CH:19]2[CH2:18][CH2:17][N:16]([CH2:15][C:12]3[S:11][C:10]([C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][N:4]=4)=[N:14][CH:13]=3)[CH2:21][CH2:20]2)=[O:44])[CH:38]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 20501324-Aminopicolinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66989375(1-((2-(Pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methanamine Trihydrochloride

Product 1

HCID 585041694-Amino-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)picolinamideYield 11.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

The compound prepared in Example 214 (0.44 g), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.25 g), 4-aminopicolinic acid (0.18 g), 1-hyroxybenzotriazole hydrate (0.20 g) and N-ethyl-N-isopropylpropan-2-amine (1.2 ml) were combined in dimethylacetamide (8 mL) and the reaction was allowed to stir 2 days. The reaction was diluted with ethyl acetate and washed with aqueous sodium bicarbonate and brine. The organic phase was dried over magnesium sulfate, filtered, concentrated and purified by column chromatography using an eluant (2 to 6% methanol/dichloromethane) to provide the title compound (0.05 g) with the following physical data.

Workup

  1. washwashed with aqueous sodium bicarbonate and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-1d14aff530ac48a283d8972f76fe3314
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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