Hydrochloric Acid → HCID 178478632, compound

HRID 216878Notes

Reaction equation

HRID 216878 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]1[N:17]([CH3:18])[CH:16]=[N:15][CH:14]=1)[C:9]([CH2:19][NH:20][C:21]1[N:29]=[CH:28][N:27]=[C:26]3[C:22]=1[N:23]=[CH:24][NH:25]3)=[CH:8]2>CCO.O>[ClH:2].[ClH:1].[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]1[N:17]([CH3:18])[CH:16]=[N:15][CH:14]=1)[C:9]([CH2:19][NH:20][C:21]1[N:29]=[CH:28][N:27]=[C:26]3[C:22]=1[N:23]=[CH:24][NH:25]3)=[CH:8]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178481237HCID 178481237, compound

Product 1

HCID 178478632HCID 178478632, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
95 °C

Procedure

A mixture of 6-bromopurine (0.07844 g, 0.3942 mmol), (8-chloro-2-(1-methyl-1H-imidazol-5-yl)quinolin-3-yl)methanamine (0.1075 g, 0.3942 mmol), and N,N-diisopropylethylamine (0.2060 mL, 1.182 mmol) in 1-butanol (3.942 mL, 0.3942 mmol) was stirred at 100° C. After 16 h, the mixture was removed from the heat. The precipitate was filtered and the solid was washed with MeOH to give an off-white solid and filtrate. The off-white solid was purified by column chromatography on a 40 g of Redi-Sep™ column using 0 to 100% gradient of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 over 14 min and then 100% isocratic of CH2Cl2:MeOH:NH4OH (89:9:1) for 20 min as eluent to give an off-white solid. The off-white solid was suspended in MeOH and filtered to give N-((8-chloro-2-(1-methyl-1H-imidazol-5-yl)quinolin-3-yl)methyl)-9H-purin-6-amine as a white solid. A suspension of in N-((8-chloro-2-(1-methyl-1H-imidazol-5-yl)quinolin-3-yl)methyl)-9H-purin-6-amine (0.10596 g) in ethanol absolute (7 mL) was treated with hydrochloric acid volumetric standard, 0.5004 N solution in water (1.084 mL, 0.54322 mmol, 2 eqv.). The mixture was stirred at 95° C. oil bath for 5 min. After 5 min, the mixture became clear solution and cooled to room temperature. The cooed mixture was concentrated under reduced pressure to give a light yellow solid. The light yellow solid was dissolved in 3 mL of water, frozen, and dried on lyophilizer to give N-((8-chloro-2-(1-methyl-1H-imidazol-5-yl)quinolin-3-yl)-methyl)-9H-purin-6-amine dihydrochloride as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 9.99 (1H, br. s.), 9.34 (1H, s), 8.66 (1H, s), 8.42-8.62 (2H, m), 8.37 (1H, s), 7.99-8.07 (2H, m), 7.67 (1H, t, J=8.0 Hz), 5.19 (2H, br. s.), 4.08 (3H, s); LC-MS (ESI) m/z 391.1 [M+H]+ (Exact Mass of neutral form: 390.111).

Workup

  1. waitAfter 5 min
  2. temperaturecooled to room temperature
  3. concentrationThe cooed mixture was concentrated under reduced pressure
  4. customto give a light yellow solid
  5. temperaturefrozen
  6. customdried on lyophilizer

Sources & evidence

ORD record
ord-1d44c6a7f4814bc6845516aa6eb5863c
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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