Dichloromethane → HCID 57290459, compound

HRID 2248788Notes

Reaction equation

HRID 2248788 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]C=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].Cl[CH2:42][Cl:43]>>[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]([CH3:40])[CH3:9])=[O:39])[CH3:38])=[C:42]([Cl:43])[CH:22]=2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 57217730HCID 57217730, compound

Product 1

HCID 57290459HCID 57290459, compoundYield 60%

Procedure

N-Chlorosuccinimide (0.313 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 (0.5 g) in dichloromethane (25 ml). After 30 minutes, the solvent was evaporated, and the product isolated by flash chromatography, eluting with 3:7 ethyl acetate:toluene, to give methyl 4-[2,6-dichloro-5-[2-(N',N'-dimethylureido)propyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoate (60%) as a white solid; mp 175°-176° C.; NMR (300 MHz, DMSO-d6): 1.00 (d, 3H, CH3), 2.61 (s, 6H), 2.82 (d, 2H), 3.72 (s, 3H, CH3), 3.83 (s, 3H, OCH3), 3.85-3.96 (m, 4H), 4.00 (s, 2H), 5.91 (d, 1H, NH), 6.99 (d, 1H), 7.33 (s, 1H), 7.38-7.50 (m, 2H), 7.61 (s, 1H).

Workup

  1. customthe solvent was evaporated
  2. customthe product isolated by flash chromatography
  3. washeluting with 3:7 ethyl acetate

Sources & evidence

ORD record
ord-698538b3b90b4b3c8bf55316127ac7d4
Source dataset
uspto-grants-1991_08
Patent number
US05041460

Reaction notes

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