Diisopropylethylamine → HCID 178456071, compound

HRID 243348Notes

Reaction equation

[C:1]1([N:7]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[C@@H:16]([NH2:19])[CH2:17][CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[N:23]=[CH:24][N:25]2C1CCCCO1.CCN(C(C)C)C(C)C>C(O)CCC>[C:1]1([N:7]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[C@@H:16]([NH:19][C:21]2[N:29]=[CH:28][N:27]=[C:26]3[C:22]=2[N:23]=[CH:24][NH:25]3)[CH2:17][CH3:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (S)-1-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)propylamine (430 mg, 1.70 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (560 mg, 2.39 mmol) and DIPEA (0.54 mL, 3.07 mmol) in n-butanol (3 mL) was heated at 90° C. in a sealed vial for 16 h. After cooling to RT, the crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge and washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% 2M NH3/MeOH in DCM) to afford 169 as a white solid (136 mg, 22%). LCMS (Method K): RT 2.89 min [M+H]+ 371.1. 1H NMR (DMSO-d6, 400 MHz): δ 12.91 (1H, s), 8.30-7.70 (5H, m), 7.68-7.21 (6H, m), 5.42 (1H, s), 2.01 (2H, bs), 1.01-0.71 (3H, m).

Workup

temperatureAfter cooling to RT
customthe crude reaction mixture
washwashed with MeOH
concentrationconcentrated in vacuo
customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record: ord-7de34a06bfda433fb182f8e9ec20b69d
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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