Triethylamine → HCID 18321803, compound

HRID 1871115Notes

Reaction equation

HRID 1871115 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][CH2:13][C:14]2[N:15]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][O:27][C:28]4[CH:29]=[CH:30][CH:31]=[C:32]5[C:37]=4[N:36]=[C:35]([CH3:38])[CH:34]=[CH:33]5)[C:20]=3[Cl:39])[CH:16]=[CH:17][CH:18]=2)=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[CH3:48][C:49]1[N:57]=[CH:56][CH:55]=[CH:54][C:50]=1[C:51](Cl)=[O:52]>ClCCl>[Cl:39][C:20]1[C:21]([CH2:26][O:27][C:28]2[CH:29]=[CH:30][CH:31]=[C:32]3[C:37]=2[N:36]=[C:35]([CH3:38])[CH:34]=[CH:33]3)=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[N:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[CH2:13][NH:12][C:10](=[O:11])/[CH:9]=[CH:8]/[C:5]1[CH:6]=[N:7][C:2]([NH:1][C:51](=[O:52])[C:50]2[CH:54]=[CH:55][CH:56]=[N:57][C:49]=2[CH3:48])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18321779HCID 18321779, compoundHCID 183219202-Methylpyridine-3-carbonyl chloride--hydrogen chloride (1/1)

Product 1

HCID 18321803HCID 18321803, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-[(E)-3-(6-aminopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]pyrrole (152 mg) and triethylamine (96 mg) in dichloromethane (3 ml) was added 2-methylnicotinoyl chloride hydrochloride (115 mg) under nitrogen in ice water bath and stirred for 1 hour at the same temperature. The reaction solvent was concentrated in vacuo and the residue was dissolved in methanol. To the solution was added 1M sodium hydroxide solution (0.5 ml) and stirred for 30 minutes. The solution was evaporated and partitioned between chloroform and water. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography on silica gel (ethyl acetate) to give 1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]-2-[(E)-3-[6-[2-methylnicotinamido]pyridin-3-yl]acryloylaminomethyl]pyrrole (124 mg) as an amorphous powder.

Workup

  1. concentrationThe reaction solvent was concentrated in vacuo
  2. dissolutionthe residue was dissolved in methanol
  3. additionTo the solution was added 1M sodium hydroxide solution (0.5 ml)
  4. stirringstirred for 30 minutes
  5. customThe solution was evaporated
  6. custompartitioned between chloroform and water
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by preparative thin-layer chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-984c1dae91ac4927ade40e55af901bca
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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