Hydrochloric Acid → HCID 67666025, compound

HRID 1458350Notes

Reaction equation

HRID 1458350 reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=1)=[C:9]2[CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)=[O:5])[CH3:2].[ClH:38]>CO>[ClH:38].[ClH:38].[CH2:36]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]1[CH:16]=[C:17]([CH3:22])[CH:18]=[C:19]([CH3:21])[CH:20]=1)=[C:9]2[CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)=[O:5])[CH3:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 44293591HCID 44293591, compound

Product 1

HCID 67666025HCID 67666025, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 452 mg (0.914 mmol) of 2-(3,5-dimethylphenyl)-3-[2-[4-(pyridin-4-yl)butylamino]ethyl]-1H-indole-5-carboxylic acid diethylamide in 45 mL of methanol was treated with 1.83 mL (3.66 mmol) of 2N hydrochloric acid. After a few minutes, the solution was evaporated to dryness. The residue was reconcentrated from methanol and then triturated with diethyl ether. The solid was collected on a filter, washed with additional diethyl ether, and dried to give 455 mg (87%) of yellowish powder, mp 154°-157° C. 500 MHz 1H NMR (DMSO-d6) was consistent with the assigned structure.

Workup

  1. waitAfter a few minutes
  2. customthe solution was evaporated to dryness
  3. customtriturated with diethyl ether
  4. customThe solid was collected on a filter
  5. washwashed with additional diethyl ether
  6. customdried
  7. customto give 455 mg (87%) of yellowish powder, mp 154°-157° C

Sources & evidence

ORD record
ord-9d7cb179368949bf9f7020612ca192e5
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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