Diisopropylethylamine → HCID 178461951, compound

HRID 243487Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH2:12])[CH3:11])[N:7]([CH3:13])[C:6]=2[C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.Cl[C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[N:24]=[CH:25][N:26]2C1CCCCO1.CCN(C(C)C)C(C)C>CC(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH:12][C:22]3[N:30]=[CH:29][N:28]=[C:27]4[C:23]=3[N:24]=[CH:25][NH:26]4)[CH3:11])[N:7]([CH3:13])[C:6]=2[C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (S)-1-(6-fluoro-1-methyl-7-pyridin-2-yl-1H-benzoimidazol-2-yl)ethylamine (100 mg, 0.37 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (88 mg, 0.37 mmol) and DIPEA (340 μL, 1.85 mmol) in IPA (5 mL) were added and the reaction mixture heated at 90° C. for 16 h. The reaction mixture was loaded onto an SCX column to remove the THP group. The column was washed with MeOH and the product was eluted with 2M NH3 in MeOH. The product fractions were collected, concentrated in vacuo and the resultant residue was subjected to flash chromatography (Si—PPC, gradient 0-5% MeOH in DCM) to give 413 as a white solid (67 mg, 47%). LCMS (Method K): RT 2.53 min [M+H]+ 389. 1H NMR (DMSO-d6, 400 MHz): δ 12.7 (1H, br s), 8.68 (1H, ddd, J=4.8, 1.7, 0.8 Hz), 8.13 (2H, d, J=21.9 Hz), 7.91 (1H, br s), 7.90 (1H, td, J=7.8, 1.8 Hz), 7.65 (1H, dd, J=8.8, 4.8 Hz), 7.60 (1H, tq, J=7.7, 1.1 Hz), 7.44 (1H, ddd, J=7.5, 4.8, 1.1 Hz), 7.10 (1H, dd, J=10.4, 8.8 Hz), 5.82-5.67 (1H, m), 3.15 (3H, s), 1.61 (3H, d, J=6.7 Hz)

Workup

additionwere added
customto remove the THP group
washThe column was washed with MeOH
washthe product was eluted with 2M NH3 in MeOH
customThe product fractions were collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f7ddf11ad5314c24b5a7949f70b49008
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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