Triethylamine → HCID 11584572, compound

HRID 1864789Notes

Reaction equation

HRID 1864789 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]3[CH:21]=[C:22]([CH2:26][NH:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[CH:23]=[N:24][CH:25]=3)=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.C(N(CC)CC)C>ClCCl>[CH3:31][N:30]([CH3:32])[CH2:29][CH2:28][N:27]([CH2:26][C:22]1[CH:23]=[N:24][CH:25]=[C:20]([C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[NH:11][CH:12]=[CH:13]3)[CH:21]=1)[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chloride2×HCID 68747834HCID 68747834, compound

Product 1

HCID 11584572HCID 11584572, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluorobenzoyl chloride (111 mg, 0.7 mmol) was added to a solution of N′-[5-(1H-indol-5-yl)-pyridin-3-ylmethyl]-N,N-dimethyl-ethane-1,2-diamine (160 mg, 0.54 mmol) and triethyl amine (109 mg, 1.08 mmol) in 15 mL of dichloromethane at room temperature. The resulting mixture was stirred at ambient temperature overnight, and then a further 111 mg of 4-fluorobenzoyl chloride was added and the mixture stirred for an additional 2 h. The volatiles were removed in vacuo to leave the crude product. Chromatography (elution with methanol/dichloromethane) provided 231 mg of material. This was dissolved in dichloromethane and washed with 1M sodium hydroxide solution. The organic phase was dried over magnesium sulfate, filtered and concentrated to leave material which was further purified by HPLC (elution with acetonitrile/water/TFA) to give 21 mg of product. LC/MS (long run): Retention time, 3.85 min; (M+H)=417.

Workup

  1. stirringthe mixture stirred for an additional 2 h
  2. customThe volatiles were removed in vacuo
  3. customto leave the crude product
  4. washChromatography (elution with methanol/dichloromethane)

Sources & evidence

ORD record
ord-57676dd72f014663a4384d2ef4c32727
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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