Hydrazine → HCID 178468659, compound

HRID 2274504Notes

Reaction equation

O=[C:2]([CH2:8][C:9](=O)[C:10]1[CH:11]=[N:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][CH:15]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:24][NH2:25]>C(O)(=O)C>[O:16]([C:13]1[N:12]=[CH:11][C:10]([C:9]2[NH:25][N:24]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:8]=2)=[CH:15][N:14]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture consisting of the solid comprising ethyl 2,4-dioxo-4-(2-phenoxypyrimidin-5-yl)butanoate (Step A, 1.00 mmol theory) in acetic acid (10 mL) was added hydrazine (0.40 mL, 410 mg, 13 mmol). The stirring mixture was heated to 60° C. for one hour and was subsequently cooled to room temperature and stirred overnight. The off-white solid which had precipitated was collected by filtration and washed with hexane. The solid was purified by silica gel flash chromatography using a 9:1 to 1:1 v/v hexane-ethyl acetate gradient through a 40-g Silicycle® flash silica cartridge to afford the title compound as a white solid (100 mg, 32% yield); Rf 0.50 with 1:1 v/v hexane-ethyl acetate; 1H-NMR (300 MHz; DMSO-d6) δ 9.12 (s, 2H), 7.50 (s, 1H), 7.43 (dd, 2H), 7.20-7.28 (m, 3H), 4.26 (q, 2H), 1.25 (t, 3H); MS (ESI−) m/z 309 (M−1); H-PGDS FPBA IC50: 1.3 μM; H-PGDS inhibitor EIA IC50: 0.13 μM.

Workup

temperaturewas subsequently cooled to room temperature
customThe off-white solid which had precipitated
filtrationwas collected by filtration
washwashed with hexane
customThe solid was purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-0cbb8450782c4329b5bb90b0c54d1b7c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126973B2

Reaction notes

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