[4-(2-Ethyl-imidazo[4,5-c]quinolin-1-yl)-butyl]-carbamic acid tert-butyl ester → 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-amine

HRID 62026Notes

Reaction equation

HRID 62026 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:14]=[C:13]1[CH2:25][CH3:26])(C)(C)C>FC(F)(F)C(O)=O>[CH2:25]([C:13]1[N:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH2:7])[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:14]=1)[CH3:26]

Participants

3

Reactant 1

HCID 22344415[4-(2-Ethyl-imidazo[4,5-c]quinolin-1-yl)-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 223444144-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-amine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [4-(2-Ethyl-imidazo[4,5-c]quinolin-1-yl)-butyl]carbamic acid tert-butyl ester of formula 5 obtained in step V in trifluroacetic acid was stirred at 40° C. for 4 hrs. Reaction mixture was then poured on ice-water mixture and extracted with chloroform. Organic layer was dried over sodium sulphate and concentrated under deduced pressure to afford 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl) butan-1-amine of formula 6.

Workup

  1. customReaction mixture
  2. additionwas then poured on ice-water mixture
  3. extractionextracted with chloroform
  4. dry with materialOrganic layer was dried over sodium sulphate
  5. concentrationconcentrated under deduced pressure

Sources & evidence

ORD record
ord-4ce514b0d1344eaaa38550503debc664
Source dataset
uspto-grants-2016_09
Patent number
US09446040B2

Reaction notes

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