Isopropylamine → HCID 57334038, compound

HRID 402344Notes

Reaction equation

HRID 402344 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.C[O:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[N:21]([CH3:31])[N:22]=[N:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:14][CH:13]=1>O1CCOCC1>[CH:1]([NH:4][C:11](=[O:10])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[N:21]([CH3:31])[N:22]=[N:23][C:24]=2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:14][CH:13]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 67498772HCID 67498772, compound

Product 1

HCID 57334038HCID 57334038, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of isopropylamine (95 μL, 1.11 mmol) in dioxane (5.5 mL) was added dropwise trimethylaluminium (2 M in heptane, 600 μL, 1.11 mmol). The resulting solution was stirred at room temperature for 1 h, then a solution of 6-(3-methyl-5-phenyl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid methyl ester (90 mg, 0.28 mmol) in dioxane (2.8 mL) was added and the reaction mixture was stirred at 90° C. for 5 h. After cooling to room temperature the mixture was poured into a Na—K-tartrate solution extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated to afford the title compound (83 mg, 85%) as a white solid. MS: m/e=352.3 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at 90° C. for 5 h
  2. temperatureAfter cooling to room temperature the mixture
  3. extractionextracted with ethyl acetate
  4. washthe combined organic extracts washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-92addc10aef74d1d92b5c60b31e9811e
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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