1-Butanol → HCID 178463555, compound

HRID 243275Notes

Reaction equation

[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH:16]([NH2:18])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:20]1[N:28]=[CH:27][N:26]=[C:25]2[C:21]=1[N:22]=[CH:23][NH:24]2.C(O)CCC>CO.C(Cl)(Cl)Cl>[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH:16]([NH:18][C:20]2[N:28]=[CH:27][N:26]=[C:25]3[C:21]=2[N:22]=[CH:23][NH:24]3)[CH3:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

1-(1-Phenyl-1H-benzoimidazol-2-yl)ethylamine from Example 4 (211 mg, 0.89 mmol) and 6-chloro-9H-purine (137 mg, 0.89 mmol) was placed in a sealed tube with n-butanol (1.7 mL) and the solution was heated to 120° C. for 48 h. The cooled suspension was diluted with MeOH/CHCl3 and the resulting solution was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 2M NH3/MeOH. The product was further purified by column chromatography (Si—PCC, gradient 0-6% MeOH in DCM) and then triturated with EtOAc to afford racemic 102 as a cream solid (190 mg, 60%). LCMS: RT 2.99 min [M+H]+ 356.2. 1H NMR (DMSO, 400 MHz): δ 8.18-8.07 (2H, m), 7.94-7.85 (1H, m), 7.71-7.45 (7H, m), 7.27-7.17 (2H, m), 7.11-7.06 (1H, m), 5.52 (1H, br), 1.57 (3H, d, J=6.83 Hz)

Workup

washThe cartridge was washed with MeOH
washthe product eluted with 2M NH3/MeOH
customThe product was further purified by column chromatography (Si—PCC, gradient 0-6% MeOH in DCM)
customtriturated with EtOAc

Sources & evidence

ORD record: ord-a46838859e5645f7bf58ad108304996e
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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