HCID 68835368, compound → HCID 68838675, compound

HRID 2112950Notes

Reaction equation

[C:1]([NH:6][NH:7][C:8]([C:10]1[N:15]2[N:16]=[C:17]([NH2:19])[N:18]=[C:14]2[CH:13]=[C:12]([Br:20])[CH:11]=1)=[O:9])(=O)[CH:2]([CH3:4])[CH3:3]>O=P(Cl)(Cl)Cl>[Br:20][C:12]1[CH:11]=[C:10]([C:8]2[O:9][C:1]([CH:2]([CH3:4])[CH3:3])=[N:6][N:7]=2)[N:15]2[N:16]=[C:17]([NH2:19])[N:18]=[C:14]2[CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product of Step 1, 2-amino-7-bromo-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid N′-isobutyryl-hydrazide (1.0 g, 2.9 mmol) was suspended in neat POCl3 (˜10 mL) and heated to 100° C. for one hour. The mixture was concentrated under reduced pressure and the residue was diluted with water. The pH of the aqueous mixture was made slightly basic by the addition of K2CO3, then extracted with a solution of 9:1 CH2Cl2/MeOH (50 mL). The organics were dried with MgSO4 and concentrated under reduced pressure to give a solid, which was triturated with ether and collected by filtration andried under vacuum to give 7-bromo-5-(5-isopropyl-[1,3,4]oxadiazol-2-yl)-[1,2,4]triazolo[1,5,a]pyridine-2-ylamine, that was used without further purification in Step 3. MS (APCI+): m/z 325.0.

Workup

concentrationThe mixture was concentrated under reduced pressure
additionthe residue was diluted with water
additionThe pH of the aqueous mixture was made slightly basic by the addition of K2CO3
extractionextracted with a solution of 9:1 CH2Cl2/MeOH (50 mL)
dry with materialThe organics were dried with MgSO4
concentrationconcentrated under reduced pressure
customto give a solid, which
customwas triturated with ether
filtrationcollected by filtration andried under vacuum

Sources & evidence

ORD record: ord-41279c430b254e2d905d7748732b23c3
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524860B2

Reaction notes

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