Ethylamine → HCID 60133236, compound

HRID 2353389Notes

Reaction equation

HRID 2353389 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[B:11]1[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]1.Cl.C[N:22](C)[CH2:23][CH2:24]CN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N)C>O1CCCC1.C(Cl)(Cl)Cl.O>[CH2:23]([NH:22][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([B:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]2)[CH:4]=1)[CH3:24]

Participants

8

Reactant 4

HCID 6341EthylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 160860864-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Product 1

HCID 60133236HCID 60133236, compoundYield 94.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (1.3 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.44 g) and 3H-[1,2,3] 1-hydroxy-7-azabenzotriazole (0.077 g) was added to a stirred solution of ethylamine in tetrahydrofuran (2M, 5 ml) in chloroform (30 ml) and the mixture was stirred for 24 h. The mixture was poured into water, passed through a hydrophobic filter tube and the organic phase was concentrated under vacuum. The residual solid was purified on an SCX cartridge eluting with methanol to give the title compound as a pale yellow solid (1.36 g).

Workup

  1. custompassed through a hydrophobic filter tube
  2. concentrationthe organic phase was concentrated under vacuum
  3. customThe residual solid was purified on an SCX cartridge
  4. washeluting with methanol

Sources & evidence

ORD record
ord-6939b00b06084011b7a21fcf0326af27
Source dataset
uspto-grants-2010_07
Patent number
US07750026B2

Reaction notes

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