HCID 86725315, compound → HCID 76684262, compound

HRID 925203Notes

Reaction equation

C(OC([N:6]1[CH2:25][CH2:24][C:10]2[C:11]3[CH:12]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=O)C>C(O)(=O)C.Br>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH:12]2[C:11]3[C:10]4[CH2:24][CH2:25][NH:6][CH2:7][CH2:8][C:9]=4[CH:17]=[CH:16][C:15]=3[CH2:14][CH2:13]2)[CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Into a glass vial, the product from step (c) in 2.5 ml acetic acid and 2.5 ml HBr (33% in acetic acid) was added. The stirred reaction mixture was heated at 60° C. for 6 hours. The reaction mixture was cooled and the volatiles were evaporated in vacuo. The residue was dissolved in water (25 ml) and washed with diethyl ether (3×). The aqueous layer was basified with 2M NaOH to pH 10 and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the title compound as a colorless oil (35 mg). 1H NMR (300 MHz, CDCl3) δ 8.43-8.38 (m, 2H); 7.22-7.12 (m, 2H); 7.08-7.00 (m, 2H); 4.49 (dd, J=8.7 Hz, 2.7 Hz, 1H); 3.10-2.82 (m, 6H); 2.73-2.45 (m, 5H); 2.04-1.93 (m, 2H); MS: ESI (positive): 265 (M+1).

Workup

customThe stirred reaction mixture
temperatureThe reaction mixture was cooled
customthe volatiles were evaporated in vacuo
dissolutionThe residue was dissolved in water (25 ml)
washwashed with diethyl ether (3×)
extractionextracted with DCM (3×)
washThe combined DCM extracts were washed with brine
dry with materialdried over Na2SO4, and solvent
customevaporated in vacuo

Sources & evidence

ORD record: ord-fdff4b4965794e0786de280246a3ddfe
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284277B2

Reaction notes

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