Triethylamine → HCID 178481036, compound

HRID 579462Notes

Reaction equation

HRID 579462 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH:15]([C:17]1[C:22]2[NH:23][C:24]([C:26]3[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=3)=[N:25][C:21]=2[CH:20]=[CH:19][C:18]=1[OH:35])=[O:16].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(=O)(O)[O-].[Na+].O1CCCC1>[OH:35][C:18]1[CH:19]=[CH:20][C:21]2[N:25]=[C:24]([C:26]3[CH:34]=[CH:33][C:29]([C:30]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[O:31])=[CH:28][CH:27]=3)[NH:23][C:22]=2[C:17]=1[CH:15]=[O:16]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178519904HCID 178519904, compound

Product 1

HCID 178481036HCID 178481036, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To dry tetrahydrofuran (5 mL), 1-methylpiperazine (69 μL, 63 mg, 0.62 mmol), triethylamine (196 μL, 142 mg, 1.40 mmol), 4-(7-Formyl-6-hydroxy-1H-benzoimidazol-2-yl)-benzoic acid (80 mg, 0.28 mmol), 1-hydroxybenzotriazole (84 mg, 0.62 mmol) and 1-ethyl-3-(dimethylaminopropyl)-carbodiimide hydrochloride (120 mg, 0.62) were added in the above order. The mixture was stirred at room temperature overnight. The resulted brown solution was suspended in saturated sodium bicarbonate (60 mL) and extracted with dichloromethane (3×20 mL). The combined organic layers were dried (Na2SO4), evaporated and purified by column chromatography (Kieselgel 60), eluting with chloroform-methanol 9:1. The title compound (35 mg, 0.096 mmol, 34%) was isolated as a white powder.

Workup

  1. extractionextracted with dichloromethane (3×20 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. customevaporated
  4. custompurified by column chromatography (Kieselgel 60)
  5. washeluting with chloroform-methanol 9:1

Sources & evidence

ORD record
ord-4219f47315be42209508124089360440
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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