Diisopropylethylamine → HCID 178425450, compound

HRID 243354Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (S)-1-(3-m-tolyl-3H-imidazo[4,5-b]pyridin-2-yl)ethylamine (420 mg, 1.66 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (550 mg, 2.33 mmol) and DIPEA (0.52 mL, 3.00 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 0-10% 2M NH3/MeOH in DCM) to afford 177 as a white solid (190 mg, 31%). LCMS (Method K): RT 2.84 min [M+H]+ 371.0. 1H NMR (DMSO-d6, 400 MHz): δ 12.90 (1H, s), 8.33-7.77 (5H, m), 7.45-7.14 (5H, m), 5.56 (1H, br), 2.25 (3H, s), 1.58 (3H, d, J=6.81 Hz). Broad signals due to presence of rotamers/tautomers

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 0-10% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record: ord-f55ad6dd49fd4b8899251b4fea329715
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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