HCID 178495885, compound → 9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine

HRID 1046992Notes

Reaction equation

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

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of N-(2,2-dimethoxyethyl)-11H-pyrido[2,3-b][1,4]benzodiazepin-6-amine (4.21 g, 14 mmol) and acetic acid (20 mL) was heated to 105° C. for 13 hours. After cooling to room temperature the solvent was removed under reduced pressure. The resulting crude product was diluted with acetone and filtered by suction to give a dark pink solid (74%). 1H NMR (DMSO-d6) 400 MHz δ: 8.53 (s, 1H), 8.15 (dd, J=4.6, 1.7 Hz, 1H), 7.85 (dd, J=7.7, 1.4 Hz, 1H), 7.77 (dd, J=7.7, 1.4 Hz, 1H), 7.63 (d, J=1.2 Hz, 1H), 7.28 (td, J=8.0, 1.7 Hz, 1H), 7.24 (d, J=1.7 Hz, 1H), 7.19 (dd, J=8.0, 1.2 Hz, 1H), 7.11 (dd, J=7.7, 4.6 Hz, 1H), 7.02 (td, J=7.5, 1.2 Hz, 1H); LC/MS [M+H]: 235.

Workup

temperatureAfter cooling to room temperature the solvent
customwas removed under reduced pressure
additionThe resulting crude product was diluted with acetone
filtrationfiltered by suction

Sources & evidence

ORD record: ord-cb83bc7c71c2420194b8f8b7cf969b4c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569331B2

Reaction notes

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