Diisopropylethylamine → HCID 52915083, compound

HRID 2175044Notes

Reaction equation

[C@H:1]12[N:8]([C:9]([C:11]3[C:12]([N:18]4[CH:22]=[CH:21][N:20]=[N:19]4)=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=3)=[O:10])[CH2:7][C@H:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.Cl[C:24]1[N:29]=[C:28]([CH3:30])[C:27]([CH3:31])=[C:26]([CH3:32])[N:25]=1.CCN(C(C)C)C(C)C>C(#N)C>[CH3:17][C:14]1[N:13]=[C:12]([N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)[C:11]([C:9]([N:8]2[C@H:1]3[C@H:6]([CH2:5][CH2:4][N:3]([C:24]4[N:29]=[C:28]([CH3:30])[C:27]([CH3:31])=[C:26]([CH3:32])[N:25]=4)[CH2:2]3)[CH2:7]2)=[O:10])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a microwave safe vial was added (1S,6R)-3,8-diazabicyclo[4.2.0]octan-8-yl(6-methyl-2-(1H-1,2,3-triazol-1-yl)pyridin-3-yl)methanone (80 mg, 0.27 mmol), 2-chloro-4,5,6-trimethylpyrimidine (84 mg, 0.54 mmol), ACN (3 mL) and DIPEA (0.093 mL, 0.54 mmol). The resulting mixture was heated to 180° C. in a microwave reactor. After 2 hours the mixture was cooled to ambient temperature and concentrated under reduced pressure. The crude residue was purified by reverse-phase HPLC (acidic) to yield the title compound (60.3 mg, 42%) as the TFA salt. MS (ESI) mass calcd. for C22H26N8O, 418.2; m/z found, 419.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.44-8.32 (m, 1H), 7.82-7.72 (m, 2H), 7.22-7.16 (m, 1H), 4.52-4.46 (m, 1H), 4.30 (dd, J=10.0, 9.0 Hz, 1H), 4.04 (tt, J=9.6, 4.8 Hz, 1H), 3.99-3.92 (m, 1H), 3.89-3.57 (m, 2H), 3.13-2.83 (m, 2H), 2.65-2.57 (m, 3H), 2.39-2.31 (m, 6H), 2.15-2.02 (m, 4H), 1.99-1.81 (m, 1H).

Workup

temperatureAfter 2 hours the mixture was cooled to ambient temperature
concentrationconcentrated under reduced pressure
customThe crude residue was purified by reverse-phase HPLC (acidic)

Sources & evidence

ORD record: ord-2977ba0d0d7a4f769a9916c237198f36
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062044B2

Reaction notes

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