Cyclopropanemethanamine → HCID 68851544, compound

HRID 1984644Notes

Reaction equation

HRID 1984644 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]#[C:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](O)=[O:19].F[B-](F)(F)F.[N:29]1(OC(N(C)C)=[N+](C)C)[C:33]2[CH:34]=[CH:35][CH:36]=CC=2N=N1.NCC1CC1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH:34]1([CH2:33][NH:29][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][CH:23]=[C:15]([C:14]#[C:13][C:3]3[C:4]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[N:5][O:6][C:2]=3[CH3:1])[CH:16]=2)[CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 688528003-[2-(5-Methyl-3-phenyl-4-isoxazolyl)ethynyl]benzoic acid

Product 1

HCID 68851544HCID 68851544, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-benzoic acid (250 mg; 0.82 mmol) in N,N-dimethylformamide (4.8 mL) was added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (318 mg, 0.99 mmol) at 0° C. After stirring for 15 min at this temperature, aminomethylcyclopropane (86 μl, 0.99 mmol) and N-ethyldiisopropylamine (0.85 mL, 4.94 mmol) were added and the reaction mixture was allowed to warm to ambient temperature. After 1.75 h stirring at ambient temperature, it was extracted with dichloromethane (300 mL) and aqueous sodium carbonate (2 M, 75 mL). The combined organic layers were washed with brine (75 mL), dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 0:100) afforded the title compound (254 mg, 87%) as a white solid. MS: m/e=357.1 [M+H]+.

Workup

  1. additionwere added
  2. extractionit was extracted with dichloromethane (300 mL) and aqueous sodium carbonate (2 M, 75 mL)
  3. washThe combined organic layers were washed with brine (75 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 0:100)

Sources & evidence

ORD record
ord-7703a82f8dd549d9810c12b6d2487f33
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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