Diisopropylethylamine → HCID 178463585, compound

HRID 243276Notes

Reaction equation

[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O: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.CCN(C(C)C)C(C)C>C(O)CCC>[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O: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: 100 °C

Procedure

A mixture of 1-(3-phenylbenzofuran-2-yl)ethylamine Example 24 (0.706 mmol), 6-chloro-9H-purine (213 mg, 1.38 mmol) and DIPEA (0.24 mL, 1.38 mmol) in n-butanol (5 mL) was heated at 100° C. for 18 h. After cooling to RT, volatiles were removed under reduced pressure and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-5% MeOH in DCM) and then triturated from MeOH with water affording 103 as an off-white solid (107 mg, 43% over two steps). LCMS: RT 4.15 min [M+H]+ 356.1. 1H NMR (DMSO, 400 MHz): δ 8.21-7.95 (3H, m), 7.73-7.60 (3H, m), 7.58-7.49 (3H, m), 7.46-7.23 (3H, m), 5.84 (1H, s), 1.67 (3H, d, J=6.99 Hz)

Workup

temperatureAfter cooling to RT
customvolatiles were removed under reduced pressure
customthe resulting residue was purified by column chromatography (Si—PCC, gradient 0-5% MeOH in DCM)
customtriturated from MeOH with water affording 103 as an off-white solid (107 mg, 43% over two steps)

Sources & evidence

ORD record: ord-2eebdb16c17149b5b028a7669b0119b7
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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