Dimethylcarbamoyl Chloride → HCID 86753449, compound

HRID 1458345Notes

Reaction equation

HRID 1458345 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=2)[NH:12][C:11]=1[C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:38][N:39]([CH3:43])[C:40](Cl)=[O:41]>O1CCCC1>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:40]([N:39]([CH3:43])[CH3:38])=[O:41])[CH:17]=2)[NH:12][C:11]=1[C:20]1[CH:21]=[C:22]([CH3:27])[CH:23]=[C:24]([CH3:26])[CH:25]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 67656043HCID 67656043, compound

Product 1

HCID 86753449HCID 86753449, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Finely divided {2-[5-amino-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (265 mg) was suspended in dry tetrahydrofuran (5mL) and diisopropylethylamine (0.146 mL) and dimethylcarbamoyl chloride (0.077 mL) were added. The reaction mixture was stirred at room temperature for 2.5 days. The reaction mixture was concentrated on a rotary evaporator and the residues were applied to four (20×20 cm 1000μ) preparative silica gel plates and eluted with a solvent system comprising methanol and methylene chloride in the ratio (1:9 v/v). The product (299 mg) was isolated as a thick gum that solidified on prolonged standing.

Workup

  1. concentrationThe reaction mixture was concentrated on a rotary evaporator
  2. washeluted with a solvent system comprising methanol and methylene chloride in the ratio (1:9 v/v)

Sources & evidence

ORD record
ord-e615f8e156a74526b85f388489ab21dd
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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