Ethylamine hydrochloride → HCID 57377301, compound

HRID 1802145Notes

Reaction equation

HRID 1802145 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]([OH:27])=O)[CH:4]=[N:3]1.[Cl-].[Li+].Cl.[CH2:31]([NH2:33])[CH3:32].C(N(C(C)C)CC)(C)C.CCCP(=O)=O>O1CCCC1.C(OCC)(=O)C>[CH2:31]([NH:33][C:25]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[C:7]([NH:8][C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:17]=[C:11]2[CH:10]=1)=[O:24])=[O:27])[CH3:32]

Participants

8

Reactant 5

HCID 11198Ethylamine hydrochloride2×HCID 81531Diisopropylethylamine2×HCID 433294Lithium ChlorideHCID 16167369Propylphosphoric anhydride2×HCID 573789541-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 57377301HCID 57377301, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid with 1 eq. lithium chloride (54 mg, 0.133 mmol), ethylamine hydrochloride (44 mg, 0.534 mmole), diisopropyl-ethylamine (93 ul, 0.534 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 197 ul, 0.334 mmol) in tetrahydrofurane (3 ml) is stirred for 1.5 hours at 70° C. As no dissolution occurs after this time, ethylamine hydrochloride (87 mg, 1.07 mmol), diisopropylethylamine (186 ul, 1.07 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 99 ul, 0.167 mmol) are added and the mixture is stirred overnight at room temperature. The white suspension is diluted with ethyl acetate, washed once with water, once with sat. aqueous sodium bicarbonate solution, once with brine, dried with magnesium sulfate and the solvent is evaporated to dryness affording N4-ethyl-1-methyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide (30 mg, 57.7%) as a white solid. mp.: 253-5° C. MS: m/z=390.2 (M+H+).

Workup

  1. dissolutionAs no dissolution
  2. additionare added
  3. stirringthe mixture is stirred overnight at room temperature
  4. washwashed once with water, once with sat. aqueous sodium bicarbonate solution, once with brine
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent is evaporated to dryness

Sources & evidence

ORD record
ord-57f911c421224b599371564399ce7645
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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