Sodium hydride → HCID 21907329, compound

HRID 1246972Notes

Reaction equation

HRID 1246972 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])[C:5]([C:14]#[N:15])=[C:4]([C:16]2[CH:24]=[CH:23][C:19]3[O:20][CH2:21][O:22][C:18]=3[CH:17]=2)[C:3]=1[C:25]#[N:26].[H-].[Na+].C(#N)C.O.[CH:33]1(O)[CH2:36]C[CH2:34]1>>[NH2:1][C:2]1[N:7]=[C:6]([CH:8]([CH3:13])[C:9]([O:11][CH:12]2[CH2:36][CH2:33][CH2:34]2)=[O:10])[C:5]([C:14]#[N:15])=[C:4]([C:16]2[CH:24]=[CH:23][C:19]3[O:20][CH2:21][O:22][C:18]=3[CH:17]=2)[C:3]=1[C:25]#[N:26]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 12968627HCID 12968627, compoundHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 21907329HCID 21907329, compound

Procedure

Methyl 2-[6-amino-4-(1,3-benzodioxol-5-yl)-3,5-dicyano-2-pyridinyl]propionate (from Example 6) (100 mg, 0.29 mmol) in cyclobutanol (5 ml) is heated under reflux with a catalytic amount of sodium hydride for 2.5 hours. The product is isolated by RP-HPLC (Kromasil column 250 * 20 mm, C18, 10 μm; acetonitrile/water gradient: 3 minutes 10%, then within 30 minutes to 80%, flow rate: 25 ml*min−1).

Workup

  1. customThe product is isolated by RP-HPLC (Kromasil column 250 * 20 mm, C18, 10 μm
  2. custom3 minutes 10%

Sources & evidence

ORD record
ord-c0a56583e61c48299058b3d88ac777ce
Source dataset
uspto-grants-2006_10
Patent number
US07129255B2

Reaction notes

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