Azetidine → HCID 57378391, compound

HRID 1802259Notes

Reaction equation

HRID 1802259 reaction equation
[F:1][CH2:2][CH2:3][N:4]([CH3:26])[C:5]1[N:25]=[C:8]2[CH:9]=[C:10]([NH:13][C:14]([C:16]3[N:20]([CH3:21])[N:19]=[CH:18][C:17]=3[C:22](O)=[O:23])=[O:15])[CH:11]=[CH:12][N:7]2[N:6]=1.[NH:27]1[CH2:30][CH2:29][CH2:28]1.CCCP(=O)=O>O1CCCC1>[F:1][CH2:2][CH2:3][N:4]([CH3:26])[C:5]1[N:25]=[C:8]2[CH:9]=[C:10]([NH:13][C:14]([C:16]3[N:20]([CH3:21])[N:19]=[CH:18][C:17]=3[C:22]([N:27]3[CH2:30][CH2:29][CH2:28]3)=[O:23])=[O:15])[CH:11]=[CH:12][N:7]2[N:6]=1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 16167369Propylphosphoric anhydrideHCID 86666025HCID 86666025, compound

Product 1

HCID 57378391HCID 57378391, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5-(2-((2-fluoroethyl)(methyl)amino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (100 mg, 277 μmol), azetidine (74.6 μl, 1.11 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 408 μl, 692 μmol) in tetrahydrofuran (5 ml) was stirred for 18 hours at 25° C. The solvent was evaporated, the residue was triturated with sodium hydrogencarbonate solution. The precipitated solid was filtered off, washed with water and dried in vacuo affording 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid {2-[(2-fluoro-ethyl)-methyl-amino]-[1,2,4]triazolo[1,5-a]pyridin-7-yl}-amide (93 mg, 83.9%) as a white solid. mp: 236-237° C., MS: m/z=401.1 (M+H+)

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with sodium hydrogencarbonate solution
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-1671e3f4d5514f85a002038368320b80
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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