Diisopropylethylamine → HCID 86666019, compound

HRID 1802229Notes

Reaction equation

HRID 1802229 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:24])[NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:25]([OH:27])=O)[CH:4]=[N:3]1.Cl.[C@H:29]12[CH2:35][C@H:32]([NH:33][CH2:34]1)[CH2:31][O:30]2.CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:16]2[N:17]=[C:11]3[CH:10]=[C:9]([NH:8][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[CH:4][C:5]=4[C:25]([N:33]4[CH2:34][C@H:29]5[CH2:35][C@@H:32]4[CH2:31][O:30]5)=[O:27])=[O:24])[CH:14]=[CH:13][N:12]3[N:15]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochlorideHCID 677759501-methyl-5-(2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 86666019HCID 86666019, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-methyl-5-(2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (150 mg, 335 μmol), (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride (136 mg, 1.00 mmol), propylphosphonic anhydride (50% in ethyl acetate, 493 μl, 837 μmol) and N,N-diisopropylethylamine (398 μl, 2.34 mmol) in tetrahydrofuran (7.00 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 2-methyl-4-((1R,4R)-2-oxa-5-aza-bicyclo[2.2.1]heptane-5-carbonyl)-2H-pyrazole-3-carboxylic acid (2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide (79 mg, 53.1%) as a white solid. mp: 272-273° C., MS: m/z=445.1 (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-09ad731e7b1f46669a9e8ddb20e74184
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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