Aniline → HCID 58172084, compound

HRID 560186Notes

Reaction equation

HRID 560186 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[CH:12][C:11]([C:29]([OH:31])=O)=[CH:10][CH:9]=2)=[O:5].Cl.CN(C)CCCN=C=NCC.O.O[N:46]1[C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=2N=N1.NC1C=CC=CC=1>ClCCl.CS(C)=O.C(OCC)(=O)C>[CH2:2]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[CH:12][C:11]([C:29](=[O:31])[NH:46][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:49]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:1]

Participants

8

Reactant 4

HCID 6115AnilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58172016HCID 58172016, compound

Product 1

HCID 58172084HCID 58172084, compoundYield 58.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction flask equipped with a nitrogen line and a stir bar was charged with a solution of 3-(3-benzyloxycarbonylamino-propyl)-1H-indole-2,5-dicarboxylic acid 2-ethyl ester (64 mg, 0.15 mmol) in dichloromethane (2 mL) and DMSO (1 mL). 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (37.5 mg, 0.19 mmol) and 1-hydroxybenzotriazole hydrate (26.5 mg, 0.19 mmol) were added. The reaction mixture was stirred for 0.5 h. Aniline (20.5 microL, 0.23 mmol) was added and stirring continued for 48 h. The reaction mixture was diluted with ethyl acetate and washed in turn with 1N HCl. and saturated sodium carbonate. The organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated and the resulting oil was purified by flash chromatography with 50-100% ethyl acetate/hexane to give 3-(3-benzyloxycarbonylamino-propyl)-5-phenylcarbamoyl-1H-indole-2-carboxylic acid ethyl ester (44 mg, 58%).

Workup

  1. customA reaction flask equipped with a nitrogen line and a stir bar
  2. stirringstirring
  3. waitcontinued for 48 h
  4. washwashed in turn with 1N HCl
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting oil was purified by flash chromatography with 50-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-97db7e9179ee42af8c8f5ea64afeab44
Source dataset
uspto-grants-2011_11
Patent number
US08063094B2

Reaction notes

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