Diisopropylethylamine → HCID 57377411, compound

HRID 1802163Notes

Reaction equation

HRID 1802163 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:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:25](O)=[O:26])[CH:4]=[N:3]1.Cl.[O:29]1[CH2:33][CH2:32][C@H:31]([NH2:34])[CH2:30]1.C(N(C(C)C)CC)(C)C.CCCP(=O)=O>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7]([NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:17]=[C:11]3[CH:10]=2)=[O:24])=[C:5]([C:25]([NH:34][C@H:31]2[CH2:32][CH2:33][O:29][CH2:30]2)=[O:26])[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 573789541-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 57377411HCID 57377411, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (100 mg, 276 μmol), (S)-tetrahydrofuran-3-ylamine hydrochloride (68.2 mg, 552 μmol), diisopropylethylamine (193 μl, 1.1 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 407 μl, 690 μmol) in tetrahydrofurane (7 ml) is refluxed for 18 hours. The solvent is evaporated and to the residue is added sat. aqueous sodium hydrogencarbonate solution. The mixture is stirred for 20 minutes while a white solid precipitates. The solid is collected by filtration, washed with diethylether and dried affording (S)-1-methyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N4-(tetrahydrofuran-3-yl)-1H-pyrazole-4,5-dicarboxamide (118 mg, 99.1%) as a white solid. mp.: >250° C. MS: m/z=432.4 (M+H+).

Workup

  1. temperatureis refluxed for 18 hours
  2. customThe solvent is evaporated and to the residue
  3. additionis added sat. aqueous sodium hydrogencarbonate solution
  4. customprecipitates
  5. filtrationThe solid is collected by filtration
  6. washwashed with diethylether
  7. customdried

Sources & evidence

ORD record
ord-e542d1cd95744f1f9b59c22cadafca85
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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