Triethylamine → HCID 23159907, compound

HRID 2110896Notes

Reaction equation

HRID 2110896 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:11]=[C:12]([CH:26]=[CH:27][CH:28]=2)[CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([OH:25])=O)=[CH:17][CH:16]=2)=[CH:2]1.S(O)(O)(=O)=O.[NH2:34][CH2:35][C:36]#[N:37].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:11]=[C:12]([CH:26]=[CH:27][CH:28]=2)[CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23]([NH:37][CH2:36][C:35]#[N:34])=[O:25])=[CH:19][CH:20]=2)=[CH:2]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 196971Aminoacetonitrile sulfate (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11603467HCID 11603467, compound

Product 1

HCID 23159907HCID 23159907, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(4-{[3-(1-benzothiophen-3-yl)benzyl]oxy}phenyl)propanoic acid (0.20 g, 0.51 mmol), aminoacetonitrile sulfate (65 mg, 0.62 mmol), triethylamine (0.17 mL, 1.22 mmol), 1-hydroxybenzotriazole (91 mg, 0.67 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.13 g, 0.68 mmol) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, and the mixture was washed successively with aqueous citric acid solution, aqueous sodium bicarbonate and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained pale-yellow oil was crystallized from diethyl ether to give the title compound (142 mg, yield 33%) as colorless needle crystals. MS: m/z 427 (MH+).

Workup

  1. washthe mixture was washed successively with aqueous citric acid solution, aqueous sodium bicarbonate and aqueous sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained pale-yellow oil was crystallized from diethyl ether

Sources & evidence

ORD record
ord-3320faf5d3824fcabf90bbf1a2904db2
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

Loading…