Diisopropylethylamine → HCID 24739475, compound

HRID 731652Notes

Reaction equation

HRID 731652 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]2[CH:22]=1.[CH:23]1([CH2:26][C:27](O)=[O:28])[CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C.[Cl-].[Na+].O.O>CN(C=O)C>[CH:23]1([CH2:26][C:27]([NH:21][C:18]2[CH:19]=[CH:20][C:15]3[N:16]([CH:22]=[C:13]([C:3]4[C:4]([C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=5)=[N:5][O:6][C:2]=4[CH3:1])[N:14]=3)[CH:17]=2)=[O:28])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 138440Cyclopropaneacetic acidHCID 23713072Sodium chloride dihydrateHCID 24739474HCID 24739474, compound

Product 1

HCID 24739475HCID 24739475, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-6-ylamine (63.9 mg, 0.22 mmol) in DMF (0.2 mL) was added to a solution containing of cyclopropylacetic acid (20 μL, 0.22 mmol), N,N,N′,N′-tetramethyl-O-(benzotriazol-1-yl)uranium tetrafluoroborate (70.6 mg, 0.22 mmol), N,N-diisopropyl ethyl amine (129 μL, 1.0 mmol) in DMF (0.3 mL) and the resulting mixture stirred at room temperature for 2 h. The resulting mixture was then poured into a mixture of brine:water (1:1) and extracted with ethyl acetate. The combined organic layers were then washed with brine, dried over sodium sulphate and evaporated to leave a brown solid. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound (44 mg, 59%) which was obtained as a light green solid. MS: m/e=373.3 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were then washed with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customto leave a brown solid
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50)

Sources & evidence

ORD record
ord-79aa489313a9464ba125fe449905b7a0
Source dataset
uspto-grants-2009_09
Patent number
US07585874B2

Reaction notes

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