Hydrochloric Acid → HCID 23512694, compound

HRID 353894Notes

Reaction equation

HRID 353894 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:26]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[N:19]=[C:18]([NH2:27])[C:17]=2[N:16]=[C:15]1[CH2:28][CH2:29][O:30][CH3:31].Cl.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.C(OCC)C.O.C(N(CC)CC)C>[NH2:27][C:18]1[C:17]2[N:16]=[C:15]([CH2:28][CH2:29][O:30][CH3:31])[N:14]([CH2:13][CH2:12][CH2:11][NH:10][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:26]=2[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[N:19]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 22344429HCID 22344429, compound

Product 1

HCID 23512694HCID 23512694, compoundYield 57.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Benzoyl chloride (900 mg, 6.40 mmol) was added in a single portion to a cooled (0° C.) solution of 1-(3-aminopropyl)-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (1.9 g, 6.26 mmol) and triethylamine (2 mL) in 1-methyl-2-pyrrolidinone (100 mL). When analysis by HPLC indicated that the reaction was complete, it was diluted with diethyl ether (1 L). The product was salted out by adding 3.3 eq. of a 1.0 M solution of hydrochloric acid in diethyl ether. The solid was isolated by filtration and then dissolved in water. The solution was neutralized using solid potassium carbonate and then extracted with dichloromethane. The extract was concentrated under reduced pressure to provide a solid. This material was recrystallized from 1,2-dichloroethane, slurried with diethyl ether, filtered and then dried in a vacuum oven to provide 1.47 g of N-{3-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]propyl}benzamide as a white solid, m.p. 167.8-169.6° C. Analysis: Calculated for C23H29N5O2: % C, 67.05; % H, 7.22; % N, 17.00. Found: % C, 67.17; % H, 7.24; % N, 16.98.

Workup

  1. customThe solid was isolated by filtration
  2. extractionextracted with dichloromethane
  3. concentrationThe extract was concentrated under reduced pressure
  4. customto provide a solid
  5. customThis material was recrystallized from 1,2-dichloroethane
  6. filtrationfiltered
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-ca5bf7a36d3c4e1c994bb93838c20542
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Reaction notes

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