Hydrochloric Acid → HCID 67051132, compound

HRID 598384Notes

Reaction equation

HRID 598384 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)[C:20]([CH2:34][O:35][CH2:36][CH3:37])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:38]>C(O)C>[ClH:38].[ClH:38].[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[C:20]([CH2:34][O:35][CH2:36][CH3:37])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68974210HCID 68974210, compound

Product 1

HCID 67051132HCID 67051132, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl [4-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate (21.0 g) was dissolved in ethanol (100 mL) and concentrated hydrochloric acid (13.0 mL). The reaction was heated at reflux for 1 hour and then cooled to ambient temperature. A tan precipitate formed. The solid was filtered and dried under vacuum for 16 hours to yield 12.1 g of 4-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butylamine dihydrochloride as a beige solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 hour
  3. customA tan precipitate formed
  4. filtrationThe solid was filtered
  5. customdried under vacuum for 16 hours

Sources & evidence

ORD record
ord-cac26df6d8af4da2969cf3bd22f3e60c
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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