HCID 178474393, compound → HCID 178508157, compound

HRID 873031Notes

Reaction equation

[CH2:1]([C:8]1[C:9]([NH:23]C(=O)C)=[N:10][C:11]2[CH:12]=[CH:13][C:14]3[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:15]=3[C:16]=2[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[NH2:23][C:9]1[C:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:17][C:16]2[C:15]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=3[CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of the obtained crude product of N-(2-benzyl-8-hydroxybenzo[f]quinoxalin-3-yl)acetamide (13) in methanol (20 mL) was heated to 65° C. and stirred overnight (14 hours). After cooling to room temperature, the solution was concentrated under reduced pressure and the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=1/1→1/10) to give 3-amino-2-benzylbenzo[f]quinoxalin-8-ol (14, v-coelenteramine) (51.3 mg, 170 mmol, quant., two steps) as an ocherous solid. TLC Rf=0.34 (n-hexane/ethyl acetate=1/1); 1H NMR (500 MHz, CD3OD) δ 4.33 (s, 2H), 7.16-7.20 (m, 2H), 7.21-7.26 (m, 1H), 7.30-7.38 (m, 5H), 7.50 (d, 1H, J=9.0 Hz), 7.76 (d, 1H, J=9.0 Hz), 8.77 (d, 1H, J=9.0 Hz).

Workup

temperatureAfter cooling to room temperature
concentrationthe solution was concentrated under reduced pressure
customthe residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=1/1→1/10)

Sources & evidence

ORD record: ord-8c2a3059a1c5464a997e136e67b9c83b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975403B2

Reaction notes

Loading…