Triethylamine → HCID 118159379, compound

HRID 713210Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[CH:8]=[N:9][CH:10]=[CH:11][C:5]2=[N:4][C:3]=1[N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[CH2:14][CH2:13]1.Cl.[O:28]1[CH2:32][CH2:31][C@H:30]([NH2:33])[CH2:29]1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[O:18][CH:15]1[CH2:16][CH2:17][N:12]([C:3]2[N:4]=[C:5]3[CH:11]=[CH:10][N:9]=[CH:8][C:6]3=[N:7][C:2]=2[NH:33][C@H:30]2[CH2:31][CH2:32][O:28][CH2:29]2)[CH2:13][CH2:14]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 3-chloro-2-(4-(2,4-difluorophenoxyl)piperidin-1-yl)pyrido[3,4-b]pyrazine (2.5 g, 6.64 mmol) in DMF (30 mL) was added (S)-tetrahydrofuran-3-amine hydrochloride (4.10 g, 33.2 mmol) and Et3N (9.25 mL, 66.4 mmol) at room temperature. The reaction mixture was stirred at 70° C. for 14 h then cooled to room temperature and diluted with EtOAc (80 mL), washed with water (30 mL) and brine (2×30 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo, then the residue was purified by column chromatography (petroleum ether:EtOAc from 10:1 to 1:1) on silica gel to give the title compound as a yellow solid (2.0 g). ESI-MS m/z [M+H]+ 428.1.

Workup

temperaturethen cooled to room temperature
washwashed with water (30 mL) and brine (2×30 mL)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customthe residue was purified by column chromatography (petroleum ether:EtOAc from 10:1 to 1:1) on silica gel

Sources & evidence

ORD record: ord-3e97645f981a482d95d6c1139ba61404
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181249B2

Reaction notes

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