Triethylamine → HCID 68898138, compound

HRID 2203535Notes

Reaction equation

HRID 2203535 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][S:30]([CH3:33])(=[O:32])=[O:31].C(N(CC)CC)C>>[N+:19]([C:14]1[CH:15]=[N:16][C:17]2[C:12]([C:13]=1[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:18]=2)([O-:21])=[O:20]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinolineHCID 21984197N-(4-aminobutyl)methanesulfonamide hydrochloride

Product 1

HCID 68898138HCID 68898138, compoundYield 82.5%

Procedure

A modification of the method described in Part E of Example 1 was used to treat 7-benzyloxy-4-chloro-3-nitroquinoline (14.4 g, 45.8 mmol) with N-(4-aminobutyl)methanesulfonamide hydrochloride (10.2 g, 50.4 mmol) and triethylamine (19.2 mL, 137 mmol). The reaction mixture was concentrated under reduced pressure, and the residue was triturated with water while heating at reflux. The resulting solid was isolated by filtration, washed with water and diethyl ether (2×100 mL), and dried under high vacuum to provide 16.8 g of N-[4-(3-nitro-7-benzyloxyquinolin-4-ylamino)butyl]methanesulfonamide as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with water
  3. temperaturewhile heating
  4. temperatureat reflux
  5. customThe resulting solid was isolated by filtration
  6. washwashed with water and diethyl ether (2×100 mL)
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-dcdbcac9dfb749a5a4108117d7f2f96e
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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