Diisopropylethylamine → HCID 178448314, compound

HRID 242960Notes

Reaction equation

[NH2:1][C@@H:2]([CH:19]([CH3:21])[CH3:20])[C:3]([NH:5][C:6]1[C:7]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:4].Cl[C:23]1[N:31]=[CH:30][N:29]=[C:28]2[C:24]=1[N:25]=[CH:26][N:27]2C1CCCCO1.CCN(C(C)C)C(C)C>C(O)CCC>[CH3:20][CH:19]([CH3:21])[C@H:2]([NH:1][C:23]1[N:31]=[CH:30][N:29]=[C:28]2[C:24]=1[N:25]=[CH:26][NH:27]2)[C:3]([NH:5][C:6]1[C:7]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (S)-2-amino-3-methyl-N-(2-phenylaminopyridin-3-yl)butyramide (3.0 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (720 mg, 3.0 mmol) and DIPEA (2.6 mL, 15.0 mmol) in n-butanol (12 mL) was heated at 100° C. for 18 h in a sealed vial. After cooling to RT, the volatiles were removed in vacuo and the resulting residue loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined, concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford the title compound (821 mg, 68% over two steps). LCMS (Method J): RT 1.75 min [M+H]+ 403.2.

Workup

temperatureAfter cooling to RT
customthe volatiles were removed in vacuo
washThe cartridge was washed 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-f78315bb70454ac899ef59fda0a3f806
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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