Hydrogen Bromide → HCID 58266732, compound

HRID 1888561Notes

Reaction equation

C[O:2][C:3]1[N:11]=[CH:10][C:9]2[NH:8][C:7]3[N:12]=[CH:13][C:14]([C:16]4[CH:21]=[CH:20][C:19]([CH2:22][N:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)=[CH:18][CH:17]=4)=[CH:15][C:6]=3[C:5]=2[CH:4]=1.Br>>[O:2]=[C:3]1[NH:11][CH:10]=[C:9]2[C:5]([C:6]3[CH:15]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([CH2:22][N:23]5[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]5)=[CH:20][CH:21]=4)[CH:13]=[N:12][C:7]=3[NH:8]2)=[CH:4]1

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 58266545HCID 58266545, compound

Product 1

HCID 58266732HCID 58266732, compoundYield 30%

Conditions

Temperature: 100 °C

Procedure

To 6-methoxy-3-(4-piperidin-1-ylmethyl-phenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (200 mg, 0.5 mmol) was added HBr (33% in acetic acid, 5 mL) and the reaction was heated at 100° C. for 16 h. The cooled reaction mixture was then evaporated in vacuo to afford a residue that was purified by preparative HPLC [0-30% MeCN in water (0.1% formic acid) over 30 min, 35 mL/min] to afford the title compound as a bright yellow solid (50 mg, 30%). 1H NMR (DMSO-D6, 400 MHz): 11.51 (s, 1H), 8.91-8.74 (m, 2H), 8.28 (s, 1H), 7.72 (d, J=8.2 Hz, 2H), 7.41 (d, J=8.1 Hz, 2H), 7.29 (s, 1H), 6.68-6.44 (s, 1H), 3.48 (s, 2H), 2.36 (s, 4H), 1.51 (m, 4H), 1.40 (m, 2H). LCMS (Method D): RT=4.97 min, M+H+=359.

Workup

customThe cooled reaction mixture
customwas then evaporated in vacuo
customto afford a residue that
customwas purified by preparative HPLC [0-30% MeCN in water (0.1% formic acid) over 30 min, 35 mL/min]

Sources & evidence

ORD record: ord-5ca610686ac54e21bcfa06dea497a435
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501765B2

Reaction notes

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