Diisopropylethylamine → HCID 178427375, compound

HRID 242848Notes

Reaction equation

[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:8]=2[CH:26]([NH2:28])[CH3:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:30]1[N:38]=[CH:37][N:36]=[C:35]2[C:31]=1[N:32]=[CH:33][NH:34]2.CCN(C(C)C)C(C)C>C(O)CCC>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)(=[O:17])=[O:18])[C:8]=2[CH:26]([NH:28][C:30]2[N:38]=[CH:37][N:36]=[C:35]3[C:31]=2[N:32]=[CH:33][NH:34]3)[CH3:27])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-[3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]ethylamine (294 mg, 0.753 mmol), 6-chloro-9H-purine (140 mg, 0.903 mmol) and DIPEA (0.20 mL, 1.13 mmol) in n-butanol (1.5 mL) was stirred in a sealed tube for 56 h at 120° C. After cooling to RT, the crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-7% 2M NH3/MeOH in DCM) affording N-(1-(3-phenyl-1-tosyl-1H-indol-2-yl)ethyl)-9H-purin-6-amine as a yellow solid (350 mg, 91%). LCMS: RT 3.31 min [M+H]+ 509.1

Workup

temperatureAfter cooling to RT
customthe crude reaction mixture
washwas washed with MeOH
washthe product eluted with 2M NH3/MeOH
additionThe product containing fractions
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-7% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record: ord-92e561c1df41424e962dafeeaf7e1966
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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