Acetic Anhydride → N-[4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-(tetrahydro-3-thienyl)acetamide

HRID 62028

Reaction equation

HRID 62028 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]2[CH2:25][CH2:24][S:23][CH2:22]2)[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1)[CH3:2].C(N(CC)CC)C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>ClCCl>[CH2:1]([C:3]1[N:4]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]([CH:21]2[CH2:25][CH2:24][S:23][CH2:22]2)[C:33](=[O:35])[CH3:34])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67145397[4-(2-Ethyl-imidazo[4,5-c]quinolin-1-yl)-butyl]-(tetrahydro-thiophen-3-yl)-amine

Product 1

HCID 67144775N-[4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-(tetrahydro-3-thienyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [4-(2-Ethyl-imidazo[4,5-c]quinolin-1-yl)-butyl]-(tetrahydro-thiophen-3-yl)-amine in dichloromethane was added triethyl amine (1.5 eq.) and acetic anhydride (1.5 eq.) and stirred at ambient temperature for 4 hrs. Reaction mixture was then diluted with dichloromethane and washed with saturated sodium bicarbonate solution. Organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford N-[4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-(tetrahydro-3-thienyl) acetamide.

Workup

  1. customReaction mixture
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialOrganic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45b40ab59b8142babf8fa7611eee21ce
Source dataset
uspto-grants-2016_09
Patent number
US09446040B2

Linked notes

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