Hydrochloric Acid → N-(1-benzyl-4,6-dichloro-1H-indol-2-ylmethyl)-N'-(4-methoxyquinolin-2-yl)propane-1,3-diamine

HRID 2415129Notes

Reaction equation

HRID 2415129 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([NH:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C:20]2[N:21]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:22]3[C:27]([CH:28]=2)=[C:26]([Cl:29])[CH:25]=[C:24]([Cl:30])[CH:23]=3)=O)[CH:4]=1.Cl>O1CCCC1>[CH2:31]([N:21]1[C:22]2[C:27](=[C:26]([Cl:29])[CH:25]=[C:24]([Cl:30])[CH:23]=2)[CH:28]=[C:20]1[CH2:18][NH:17][CH2:16][CH2:15][CH2:14][NH:13][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86591639HCID 86591639, compound

Product 1

HCID 69843219N-(1-benzyl-4,6-dichloro-1H-indol-2-ylmethyl)-N'-(4-methoxyquinolin-2-yl)propane-1,3-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-benzyl-4,6-dichloro-1H-indole-2-carboxylic acid [3-(4-methoxy-quinolin-2-ylamino)-propyl]-amide (200 mg, 0.37 mmol) [from example 12] in anhydrous tetrahydrofuran (15 ml) was treated with 1 N borane-tetrahydrofuran complex (1.1 ml, 1.1 mmol). The solution was heated a reflux for 24 hours then cooled to ambient temperature. Treated with the dropwise addition of concentrated hydrochloric acid (1 ml) then stirred for 1 hour. Evaporated under reduced pressure to a residue and taken into a system of saturated aqueous sodium chloride (20 ml) and 10% sodium hydroxide (20 ml). Extracted into ethyl acetate. The extracts were dried (sodium sulfate) then evaporated to an oil. Column chromatography on silica (95/5 methylene chloride/methanolic ammonia) gave N-(1-benzyl-4,6-dichloro-1H-indol-2-ylmethyl)-N′-(4-methoxyquinolin-2-yl)propane-1,3-diamine as a colorless resin. This was taken into chloroform (5 ml) then treated with 4N hydrogen chloride in 1,4-dioxane (300 μl). Evaporation under reduced pressure gave N-(1-benzyl-4,6-dichloro-1H-indol-2-ylmethyl)-N′-(4-methoxyquinolin-2-yl)propane-1,3-diamine dihydrochloride (102 mg, 42%) as a white solid. [M+H]+ 519.

Workup

  1. temperatureThe solution was heated
  2. temperaturea reflux for 24 hours
  3. customEvaporated under reduced pressure to a residue
  4. extractionExtracted into ethyl acetate
  5. dry with materialThe extracts were dried (sodium sulfate)
  6. customthen evaporated to an oil

Sources & evidence

ORD record
ord-74bc9755c8114c31ac8daa9b2ec4a057
Source dataset
uspto-grants-2004_11
Patent number
US06818655B2

Reaction notes

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