Chlorosuccinimide → HCID 57002054, compound

HRID 2248786Notes

Reaction equation

HRID 2248786 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][N:10]([CH3:40])[C:11](=[O:39])[NH:12][CH:13]([CH3:38])[CH2:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH3:24])[CH:19]=[C:18]2[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=1[O:36][CH3:37]>ClCCl>[Cl:1][C:19]1[N:20]([CH3:24])[C:21]2[C:17]([C:18]=1[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=1[O:36][CH3:37])=[CH:16][C:15]([CH2:14][CH:13]([NH:12][C:11]([N:10]([CH3:9])[CH3:40])=[O:39])[CH3:38])=[CH:23][CH:22]=2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57217730HCID 57217730, compound

Product 1

HCID 57002054HCID 57002054, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Chlorosuccinimide (0.437 g) was added in one portion to a stirred solution of methyl 4-[5-[2-(N',N'-dimethylureido)propyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoate (1.3 g) in dry dichloromethane (25 ml), under a nitrogen atmosphere. After 10 minutes, the solvent was evaporated, and the product purified by flash chromatography, eluting with 3:7 ethyl acetate:toluene, to give, after crystallization from ethyl acetate, methyl 4-[2-chloro-5-[2-(N',N'-dimethylureido)propyl]-1-methylindol-3-ylmethyl]-3methoxybenzoate (45%) as a white solid; mp 148° C.; NMR (300 MHz, DMSO-d6). 0.96 (d, 3H, CH3), 2.50-2.60 (m, 1H), 2.68 (s, 6H), 2.75-2.85 (m, 1H), 3.68-3.86 (m, 7H), 3.93 (s, 3H, OCH3), 4.02 (s, 2H), 5.87 (d, 1H, NH), 6.95-7.05 (m, 2H), 7.19 (s, 1H), 7.37 (d, 1H), 7.40-7.55 (m, 2H).

Workup

  1. customthe solvent was evaporated
  2. customthe product purified by flash chromatography
  3. washeluting with 3:7 ethyl acetate
  4. customtoluene, to give
  5. customafter crystallization from ethyl acetate, methyl 4-[2-chloro-5-[2-(N',N'-dimethylureido)propyl]-1-methylindol-3-ylmethyl]-3methoxybenzoate (45%) as a white solid

Sources & evidence

ORD record
ord-01438b29ca1a4b858a6816116b411c3f
Source dataset
uspto-grants-1991_08
Patent number
US05041460

Reaction notes

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