Sodium Chloride → HCID 59568420, compound

HRID 1695489Notes

Reaction equation

HRID 1695489 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][NH:14][C:15]3[CH:16]=[C:17]([C:21]([OH:23])=O)[N:18]([CH3:20])[N:19]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.[OH:45][C:46]([CH3:50])([CH3:49])[CH2:47][NH2:48].[Cl-].[Na+]>CN(C=O)C>[OH:45][C:46]([CH3:50])([CH3:49])[CH2:47][NH:48][C:21]([C:17]1[N:18]([CH3:20])[N:19]=[C:15]([NH:14][CH2:13][C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][O:10][C:11]=2[CH3:24])[CH:16]=1)=[O:23]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 27960291-Hydroxybenzotriazole hydrateHCID 66643816HCID 66643816, compound

Product 1

HCID 59568420HCID 59568420, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2-methyl-2H-pyrazole-3-carboxylic acid (0.212 mmol) in DMF (5 mL) was added 1-hydroxybenzotriazole hydrate (0.318 mmol), N-ethyldiisopropylamine (0.848 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimidazole hydrochloride (0.318 mmol) and 2-hydroxy-2-methylpropylamine (0.318 mmol) and the resulting mixture stirred overnight at room temperature. The reaction mixture was then poured into aqueous sodium chloride (saturated) and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution and then dried over sodium sulfate, filtered and evaporated. Concentration and purification by preparative HPLC afforded the title compound (13 mg, 14%) as an off white solid. MS: m/e=402.2 [M+H]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. concentrationConcentration and purification by preparative HPLC

Sources & evidence

ORD record
ord-466c745703b84f6d86d735c2d88fc659
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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