Diisopropylethylamine → HCID 178461966, compound

HRID 242993Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (S)-2-amino-N-[4-fluoro-2-(6-fluoropyridin-3-ylamino)phenyl]propionamide (193 mg, 0.66 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (165 mg, 0.69 mmol) and DIPEA (0.34 mL, 1.98 mmol) in n-butanol (1 mL) was heated at 100° C. in a sealed vial for 16 h. After cooling to RT, the volatiles were removed in vacuo and the resulting residue loaded onto an Isolute® SCX-2 cartridge then washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo to afford the title compound as a red solid (255 mg, 94%). LCMS (Method C): RT 2.40 min [M+H]+ 411.2.

Workup

temperatureAfter cooling to RT
customthe volatiles were removed in vacuo
washthen washed with MeOH
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-abd65d9cbb7b48bcac94dee2308fb5e5
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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