Hydrochloric Acid → HCID 178423526, compound

HRID 717131Notes

Reaction equation

[ClH:1].[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[N:13](C3CCCCO3)[CH:12]=[N:11][N:10]=2)[CH:6]=[CH:5][C:4]=1[C:20]1[N:25]=[C:24]2[NH:26][C:27](=[O:30])[CH2:28][NH:29][C:23]2=[N:22][CH:21]=1>C(O)C>[ClH:1].[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[NH:13][CH:12]=[N:11][N:10]=2)[CH:6]=[CH:5][C:4]=1[C:20]1[N:25]=[C:24]2[NH:26][C:27](=[O:30])[CH2:28][NH:29][C:23]2=[N:22][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Hydrochloric acid (6 N in water 0.149 mL, 0.894 mmol) was added to a stirred mixture of 7-(2-methyl-4-(4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazol-3-yl)phenyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (0.070 g, 0.179 mmol) in ethanol (3 mL) at 80° C. The system was purged with nitrogen. The resulting mixture was sealed and heated at 80° C. The resulting mixture was heated at 80° C. for 25 min and then cooled to room temperature. Solids were collected by filtration, washed with methanol and dried under high vacuum at 40° C. to give the desired product (0.058 g, 0.169 mmol, 94% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 11.32 (s, 1H), 8.66 (s, 1H), 7.97 (s, 1H), 7.92 (dd, J=1.37, 7.97 Hz, 1H), 7.74 (s, 1H), 7.50 (d, J=7.97 Hz, 1H), 4.14 (s, 2H), 2.44 (s, 3H); MS (ESI) m/z 308.3 [M+1]+.

Workup

customThe system was purged with nitrogen
customThe resulting mixture was sealed
temperatureThe resulting mixture was heated at 80° C. for 25 min
temperaturecooled to room temperature
filtrationSolids were collected by filtration
washwashed with methanol
customdried under high vacuum at 40° C.

Sources & evidence

ORD record: ord-1152d53fa9f14a3da9d38427703cd58b
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193692B2

Reaction notes

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