HCID 178472771, compound → HCID 178525918, compound

HRID 2410061Notes

Reaction equation

[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14]([NH:16][CH2:17][C:18]([O:20]CC)=[O:19])=[O:15])=[C:10]([OH:23])[N:9]([CH:24]3[CH2:29][CH2:28][CH2:27][N:26](C(OCC4C=CC=CC=4)=O)[CH2:25]3)[C:8]2=[O:40])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(=O)C.Br.O>[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])=[C:10]([OH:23])[N:9]([CH:24]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]3)[C:8]2=[O:40])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

N-{[3-Cyclohexyl-6-hydroxy-2,4-dioxo-1-(3-piperidinyl)-1,2,3,4-tetrahydro-5-pyrimidinl]carbonyl}glycine hydrobromide. Phenylmethyl 3-[3-cyclohexyl-5-({[2-(ethyloxy)-2-oxoethyl]amino}carbonyl)-6-hydroxy-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-1-piperidinecarboxylate (1.2 g, 2.15 mmoles) was stirred in a mixture of acetic acid (30 mL) and 48% hydrobromic acid (5.0 mL) for 40 hours—reaction incomplete. The mixture was then heated at 60° C. for 2 hours, diluted with water and extracted with ethyl acetate (×5). The combined extracts were dried and evaporated, and recrystallized from diethyl ether-hexane to give the title compound (160 mg, 20%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.84 (br. s., 1 H), 10.11 (s, 1H), 8.86 (s, 1 H), 5.12 (s, 1 H), 4.63 (t, J=12.00 Hz, 1 H), 4.09 (s, 2 H), 3.66 (t, J=11.37 Hz, 1 H), 3.28 (d, J=10.61 Hz, 2 H), 2.77 (t, J=11.12 Hz, 1 H), 2.36 (dd, J=12.38, 3.54 Hz, 1 H), 2.22-2.32 (m, 2 H), 1.89 (d, J=12.63 Hz, 1 H), 1.69-1.81 (m, 4 H), 1.55-1.67 (m, 4 H), 1.27 (q, J=12.88 Hz, 2 H), 1.11 (q, J=12.97 Hz, 1 H)

Workup

customreaction incomplete
extractionextracted with ethyl acetate (×5)
customThe combined extracts were dried
customevaporated
customrecrystallized from diethyl ether-hexane

Sources & evidence

ORD record: ord-35b8785685ee49a1af424d9555a66ff8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815884B2

Reaction notes

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