2-Aminopyridine → HCID 20622841, compound

HRID 2121135Notes

Reaction equation

HRID 2121135 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](O)=[O:15])=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ON1C(=O)C2C=CC=CC=2N=N1.[NH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)=[O:15])=[CH:9][C:8]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 104392-AminopyridineHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20622826HCID 20622826, compound

Product 1

HCID 20622841HCID 20622841, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the resultant acid from Example 62B (1.0 equivalent) in dimethylformamide (DMF) is added 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (1.5 equivalents) followed by 2-aminopyridine (1.0 equivalent) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.5 equivalents). When judged complete by TLC analysis, the reaction is taken up in ethyl acetate which is washed with 1N HCl and saturated brine, and then is dried and evaporated. The crude reaction mixture is purified by column chromatography to afford the title product.

Workup

  1. washis washed with 1N HCl and saturated brine
  2. customis dried
  3. customevaporated
  4. customThe crude reaction mixture
  5. customis purified by column chromatography

Sources & evidence

ORD record
ord-79f0e9a47f2e48f895d9029d00168f4a
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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