Azetidine → HCID 57378180, compound

HRID 1802234Notes

Reaction equation

HRID 1802234 reaction equation
[CH2:1]([N:3]([CH3:25])[C:4]1[N:24]=[C:7]2[CH:8]=[C:9]([NH:12][C:13]([C:15]3[N:19]([CH3:20])[N:18]=[CH:17][C:16]=3[C:21]([OH:23])=O)=[O:14])[CH:10]=[CH:11][N:6]2[N:5]=1)[CH3:2].[NH:26]1[CH2:29][CH2:28][CH2:27]1.CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:1]([N:3]([CH3:25])[C:4]1[N:24]=[C:7]2[CH:8]=[C:9]([NH:12][C:13]([C:15]3[N:19]([CH3:20])[N:18]=[CH:17][C:16]=3[C:21]([N:26]3[CH2:29][CH2:28][CH2:27]3)=[O:23])=[O:14])[CH:10]=[CH:11][N:6]2[N:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 67776185HCID 67776185, compound

Product 1

HCID 57378180HCID 57378180, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(2-(ethyl(methyl)amino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (144 mg, 419 μmol), azetidine (84.8 μl, 1.26 mmol), propylphosphonic anhydride (50% in ethyl acetate, 618 μl, 1.05 mmol) and N,N-diisopropylethylamine (214 μl, 1.26 mmol) in tetrahydrofuran (7 ml) was refluxed for 2.5 days (weekend). The solvent was evaporated, the residue was triturated with sodium hydrogencarbonate solution. The precipitated solid was filtered off, washed with water and dried affording 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(ethyl-methylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide (151 mg white solid, 94.1%) as a white solid. mp: 229-232° C., MS: m/z=383.1 (M+H+)

Workup

  1. temperaturewas refluxed for 2.5 days (weekend)
  2. customThe solvent was evaporated
  3. customthe residue was triturated with sodium hydrogencarbonate solution
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-55c17a2c0d7a4732aa37c24c525c480e
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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