Ethanol → HCID 178506371, compound

HRID 216849Notes

Reaction equation

HRID 216849 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[Cl:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][C:29]([F:32])([F:31])[F:30])[C:18]([CH2:33][NH2:34])=[CH:17]2.C(N(CC)C(C)C)(C)C.C(O)C>>[Cl:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][C:29]([F:30])([F:31])[F:32])[C:18]([CH2:33][NH:34][C:2]1[N:10]=[CH:9][N:8]=[C:7]3[C:3]=1[N:4]=[CH:5][NH:6]3)=[CH:17]2

Participants

5

Reactant 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57708021HCID 57708021, compound

Product 1

HCID 178506371HCID 178506371, compound

Conditions

Temperature
75 °C

Procedure

A mixture of 6-chloropurine (0.1109 g, 0.7175 mmol), (8-chloro-2-(2-(trifluoro-methoxy)phenyl)quinolin-3-yl)methanamine (0.2531 g, 0.7175 mmol), and N,N-diisopropylethylamine (0.2500 mL, 1.435 mmol) in ethanol (4.221 mL, 0.7175 mmol) was stirred at 75° C. After 36 h, the mixture was removed from the heat and concentrated under reduced pressure. The residue was purified by flash column chromatography on a silica gel column using 50% of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 as eluent to give N-((8-chloro-2-(2-(trifluoromethoxy)phenyl)quinolin-3-yl)methyl)-9H-purin-6-amine as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.94 (1H, s), 8.38 (1H, s), 8.03-8.32 (3H, m), 7.96-8.02 (1H, m), 7.93 (1H, dd, J=7.5, 0.9 Hz), 7.51-7.75 (5H, m), 4.69 (2H, br. s.); LC-MS (ESI) m/z 471.1 [M+H]+.

Workup

  1. customthe mixture was removed from the
  2. temperatureheat
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography on a silica gel column

Sources & evidence

ORD record
ord-05567e028187481ab6ad56b33d81f4b9
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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