1-Hydroxybenzotriazole → HCID 21254076, compound

HRID 1292388Notes

Reaction equation

HRID 1292388 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15](CC)C(O)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:21]N1C2C=CC=CC=2N=N1.Cl.CN(C)[CH2:34][CH2:35][CH2:36]N=C=NCC.[NH2:43][CH2:44][CH2:45][C:46]1[C:54]2[C:49](=[CH:50][CH:51]=[C:52]([OH:55])[CH:53]=2)[NH:48][C:47]=1[C:56]1[CH:61]=[C:60]([CH3:62])[CH:59]=[C:58]([CH3:63])[CH:57]=1>C(Cl)Cl.CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:36][CH2:35][C:34]([NH:43][CH2:44][CH2:45][C:46]2[C:54]3[C:49](=[CH:50][CH:51]=[C:52]([OH:55])[CH:53]=3)[NH:48][C:47]=2[C:56]2[CH:57]=[C:58]([CH3:63])[CH:59]=[C:60]([CH3:62])[CH:61]=2)=[O:21])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 357760HCID 357760, compoundHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21254045HCID 21254045, compound

Product 1

HCID 21254076HCID 21254076, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-benzyloxyphenylbutyric acid (159 mg in a mixture of 2 mL methylene chloride and 0.5 mL N,N-dimethylformamide) was added 1-hydroxybenzotriazole (110 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (113 mg) and the reagents allowed to mix for 30 minutes. At this time a solution of 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-ol (144 mg in 4 mL N,N-dimethylformamide) was added and the reaction stirred at room temperature. After 6 hours, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (hexane:ethyl acetate, 4:5) to give the title compound (241 mg).

Workup

  1. additionto mix for 30 minutes
  2. concentrationthe mixture was concentrated in vacuo
  3. custompurified by flash chromatography on silica gel (hexane:ethyl acetate, 4:5)

Sources & evidence

ORD record
ord-4eeb403d45e947a7ae89182213452cd6
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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