Iodoacetamide → HCID 18914254, compound

HRID 1292381Notes

Reaction equation

HRID 1292381 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(N(C(C)C)CC)(C)C.I[CH2:42][C:43]([NH2:45])=[O:44]>C(#N)C.CN(C)C=O>[CH3:8][C:6]1[CH:5]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][N:20]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)[CH2:42][C:43]([NH2:45])=[O:44])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

6

Reactant 3

HCID 3727IodoacetamideHCID 81531DiisopropylethylamineHCID 9979079HCID 9979079, compound

Product 1

HCID 18914254HCID 18914254, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-[4-[[2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]amino]butyl]phenol (15 mg in a mixture of 0.7 mL acetonitrile and 0.2 mL N,N-dimethylformamide) was added 0.015 mL of diisopropylethyl amine followed by 8 mg of iodoacetamide and the mixture stirred at room temperature. After 4.5 hours the crude reaction mixture was applied to a silica gel preparative TLC plate and eluted with (methylene chloride:methanol, 93:7). Isolation of the desired band was followed by extraction with methylene chloride:methanol (95:5) and further purification of this material by flash chromatography on silica gel (hexane:ethyl acetate, 2:5) to give the title compound (16 mg). m/e=470 (M+H)

Workup

  1. customAfter 4.5 hours the crude reaction mixture
  2. washeluted with (methylene chloride:methanol, 93:7)
  3. extractionIsolation of the desired band was followed by extraction with methylene chloride:methanol (95:5) and further purification of this material by flash chromatography on silica gel (hexane:ethyl acetate, 2:5)

Sources & evidence

ORD record
ord-393281d4ff42416a916fd9230423c745
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

Loading…