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Triethylamine → 2-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid, 5-indanyl ester

HRID 1492492
Notes
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Reaction equation

HRID 1492492 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][N:19]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[C:7]([C:11]([OH:13])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[CH2:32]1[C:40]2[C:35](=[CH:36][C:37](O)=[CH:38][CH:39]=2)[CH2:34][CH2:33]1.CNC1C=CC=C(NC)N=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][N:19]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[C:7]([C:11]([O:13][C:37]2[CH:36]=[C:35]3[C:40](=[CH:39][CH:38]=2)[CH2:32][CH2:33][CH2:34]3)=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 151185-IndanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111943672-N,6-N-dimethylpyridine-2,6-diamineHCID 189503772-butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid

Product 1

HCID 57248162
2-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid, 5-indanyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture containing 2-butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid (903 mg, 2.03 mmol, prepared as described in part C of Example 9), 5-indanol (307 mg, 2.29mmol), 2,6-dimethylaminopyridine (50.8 mg, 0.416 mmol) and triethylamine (0.377 mL, 2.70 mmol) in 9 mL of dichloromethane cooled in an ice bath was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (519 mg, 2.70 mmol). The stoppered reaction mixture was allowed to warm to ambient temperature overnight, then diluted with methylene chloride and rinsed with water and saturated aqueous sodium chloride solution. The organic extract was dried over anhydrous magnesium sulfate and concentrated in vacuo to give 1.83 g of crude product. Flash chromatography on 75 g of silica gel eluted with 8:2, hexanes:ethyl acetate gave 1.03 g of the title A compound.

Workup

  1. temperaturecooled in an ice bath
  2. customThe stoppered reaction mixture
  3. washrinsed with water and saturated aqueous sodium chloride solution
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give 1.83 g of crude product
  8. washFlash chromatography on 75 g of silica gel eluted with 8:2, hexanes
  9. customethyl acetate gave 1.03 g of the title A compound

Sources & evidence

ORD record
ord-de562a164a004bcc8b6cb31711508a92
Source dataset
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05374615

Reaction notes

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