Diisopropylethylamine → HCID 54193132, compound

HRID 1458338Notes

Reaction equation

HRID 1458338 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[CH:11][CH2:12]O)=[CH:9][C:4]=2[N:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.[CH3:23][S:24]([O:27]S(C)(=O)=O)(=O)=[O:25].[CH3:32][O:33][C:34]1[CH:35]=[C:36]([C:42]2[NH:43][C:44]3[C:49]([C:50]=2[CH2:51][CH2:52][NH2:53])=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH:37]=[CH:38][C:39]=1[O:40][CH3:41]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:32][O:33][C:34]1[CH:35]=[C:36]([C:42]2[NH:43][C:44]3[C:49]([C:50]=2[CH2:51][CH2:52][NH:53][CH2:12][CH:11]=[CH:10][C:8]2[CH:7]=[CH:6][C:5]4[N:1]([S:24]([CH3:23])(=[O:27])=[O:25])[CH:2]=[N:3][C:4]=4[CH:9]=2)=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH:37]=[CH:38][C:39]=1[O:40][CH3:41]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 368016595426-76-9HCID 178520419HCID 178520419, compound

Product 1

HCID 54193132HCID 54193132, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(1H-benzoimidazol-5-yl)-prop-2-en-1-ol (44 mg in a mixture of 2 mL methylene chloride and 0.1 mL N,N-dimethylformaminde) at 0° C. was added sequentially 346 mg of tetrabutylammonium bromide, 0.110 mL diisopropylethylamine, and 100 mg methanesulfonic anhydride and the mixture allowed to warm to room temperature. After 1 hour, this mixture was added to a solution of 2-[2-(3,4-dimethoxyphenyl)-1H-indol-3-yl]-ethylamine (300 mg in a mixture of 6 mL methylene chloride and 1.5 mL N,N-dimethylformamide) and stirring continued for 2.5 hours. At this time the mixture was concentrated in vacuo and the residue purified by flash chromatography on silica gel (methylene chloride:methanol, 91:9) to give the title compound (24 mg).

Workup

  1. waitcontinued for 2.5 hours
  2. concentrationAt this time the mixture was concentrated in vacuo
  3. customthe residue purified by flash chromatography on silica gel (methylene chloride:methanol, 91:9)

Sources & evidence

ORD record
ord-10ef1e3e2c3b4e528754b86d06c36ce7
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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