Sodium Bicarbonate → HCID 68835872, compound

HRID 2112946Notes

Reaction equation

HRID 2112946 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[N:13]2[N:14]=[C:15]([NH:17]C(NCC)=O)[N:16]=[C:12]2[CH:11]=[C:10]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH:9]=1)=[O:7])(=O)[CH3:2].C(=O)(O)[O-].[Na+]>>[CH3:2][C:1]1[O:7][C:6]([C:8]2[N:13]3[N:14]=[C:15]([NH2:17])[N:16]=[C:12]3[CH:11]=[C:10]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH:9]=2)=[N:5][N:4]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 68835349HCID 68835349, compound

Product 1

HCID 68835872HCID 68835872, compoundYield 58%

Conditions

Temperature
120 °C

Procedure

A mixture of the product of Step 2 (0.419 g, 1.10 mmol) in polyphosphoric acid (10 mL) was heated to 120° C. for 2 h. The viscous mixture was poured onto ice and made basic with saturated aqueous sodium bicarbonate, then extracted with dichloromethane (4×250 mL). Removal of the solvent in vacuo gave a solid which was triturated with methanol then filtered to give 5-(5-methyl-[1,3,4]oxadiazol-2-yl)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (0.185 g, 58%) as a solid. ACPI-MS Found: [M+H]+=294.

Workup

  1. additionThe viscous mixture was poured onto ice
  2. extractionextracted with dichloromethane (4×250 mL)
  3. customRemoval of the solvent in vacuo
  4. customgave a solid which
  5. customwas triturated with methanol
  6. filtrationthen filtered

Sources & evidence

ORD record
ord-1d3971901fa149f1ad0860a416d8c9d6
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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