Hydrochloric Acid → 1-[2,4-Dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole hydrochloride

HRID 613613Notes

Reaction equation

HRID 613613 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[N:18]=[C:17]([CH3:20])[CH:16]=[CH:15]3)=[C:6]([Cl:21])[CH:5]=[CH:4][C:3]=1[N:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][NH:28][C:29](=[O:42])[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][C:35]([C:38](=[O:41])[NH:39][CH3:40])=[CH:34][CH:33]=1.Cl>CO>[ClH:1].[Cl:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[N:18]=[C:17]([CH3:20])[CH:16]=[CH:15]3)=[C:6]([Cl:21])[CH:5]=[CH:4][C:3]=1[N:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][NH:28][C:29](=[O:42])[CH:30]=[CH:31][C:32]1[CH:33]=[CH:34][C:35]([C:38](=[O:41])[NH:39][CH3:40])=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 543680141-[2,4-Dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

Product 1

HCID 699613241-[2,4-Dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole hydrochlorideYield 172.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (35 mg) in methanol (2 ml) was added 10% solution of hydrogen chloride in methanol (0.3 ml) and allowed to stand for 10 minutes. The reaction mixture was evaporated in vacuo and hydrogen chloride was azeotropically removed with methanol. The residue was dried at ambient temperature for 6 hours in vacuo and solidified with ethyl acetate to give 1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole hydrochloride (32 mg) as an amorphous powder.

Workup

  1. customThe reaction mixture was evaporated in vacuo and hydrogen chloride
  2. customwas azeotropically removed with methanol
  3. customThe residue was dried at ambient temperature for 6 hours in vacuo

Sources & evidence

ORD record
ord-cc993c7b6ee647b79bd3b7150526bfcb
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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