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Acetic Acid → 3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole

HRID 1646770
Notes
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Reaction equation

HRID 1646770 reaction equation
[NH2:1][CH:2]([C:4]1[N:5]=[CH:6][N:7]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]=1[CH3:9])[CH3:3].[CH3:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]([S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)(=[O:41])=[O:40])[C:31]=1[CH2:48][CH:49]=O.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[CH3:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]([S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)(=[O:41])=[O:40])[C:31]=1[CH2:48][CH2:49][NH:1][CH:2]([C:4]1[N:5]=[CH:6][N:7]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:8]=1[CH3:9])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 104066724-(1-aminoethyl)-5-methyl-1-trityl-1H-imidazoleHCID 104257273-Methyl-1-(phenylsulfonyl)-2-indoleacetaldehyde

Product 1

HCID 102588713-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindoleYield 71.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-(1-aminoethyl)-5-methyl-1-trityl-1H-imidazole (735 mg), 3-methyl-1-(phenylsulfonyl)-2-indoleacetaldehyde (626 mg) and molecular sieves 3A (100 mg) in dry methanol (30 ml) was stirred at ambient temperature for 30 minutes. Acetic acid (0.35 ml) and sodium cyanoborohydride (126 mg) were added and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was treated with cold water, extracted twice with ethyl acetate, which was washed with brine and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue was chromatographed over silica gel (eluted with 3% methanol in chloroform) to give 3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole (947 mg) as an amorphous powder.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. extractionextracted twice with ethyl acetate, which
  3. washwas washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed over silica gel (eluted with 3% methanol in chloroform)

Sources & evidence

ORD record
ord-3641f44d225a4a09962507c0440ee423
Source dataset
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05180728

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes