Water → HCID 70146692, compound

HRID 442851Notes

Reaction equation

HRID 442851 reaction equation
Cl.C[N:3](C)[CH2:4][CH2:5][CH2:6]N=C=NCC.[CH3:13][O:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][O:49][CH3:50])=[CH:43][CH:42]=2)[C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[C:25]=2[C:38](O)=[O:39])=[CH:19][CH:18]=1.C(N)CC.O>C(Cl)Cl>[CH2:4]([NH:3][C:38]([C:25]1[N:26]([CH2:33][CH2:34][N:35]([CH3:36])[CH3:37])[C:27]2[C:32]([C:24]=1[CH:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][O:14][CH3:13])=[CH:18][CH:19]=1)[C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][O:49][CH3:50])=[CH:43][CH:42]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:39])[CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 7852PropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70145434HCID 70145434, compound

Product 1

HCID 70146692HCID 70146692, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (728 mg, 3.80 mmol) was added to a solution of 3-{bis[4-(methoxymethoxy)phenyl]methyl}-1-(2-dimethylaminoethyl)indole-2-carboxylic acid (1.0 g, 1.90 mmol) obtained in Example 48 and propylamine (0.23 ml, 2.85 mmol) in 10 ml of methylene chloride, followed by stirring at room temperature for 3.5 hours. Water was added to the reaction solution followed by extraction with chloroform. The resulting organic layer was washed successively with 2N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give 1.2 g (quantitative) of the title compound.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe resulting organic layer was washed successively with 2N hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium bicarbonate, and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a5fc1745e8b7495c9d36edf3e94b3f59
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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