Cyanogen Bromide → HCID 11504622, compound

HRID 2222235Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[CH2:12][N:13]1[C:21]([C:22]2[N:26]([CH3:27])[CH:25]=[C:24]([C:28]#[N:29])[CH:23]=2)=[C:20]2[C:15]([N:16]([CH2:33][CH:34]3[CH2:36][CH2:35]3)[C:17](=[O:32])[N:18]=[C:19]2[NH:30][NH2:31])=[N:14]1.[N:37]#[C:38]Br>O1CCOCC1>[NH2:37][C:38]1[N:18]2[C:17](=[O:32])[N:16]([CH2:33][CH:34]3[CH2:35][CH2:36]3)[C:15]3[C:20](=[C:21]([C:22]4[N:26]([CH3:27])[CH:25]=[C:24]([C:28]#[N:29])[CH:23]=4)[N:13]([CH2:12][C:5]4[C:4]5[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=5)[N:8]=[CH:7][CH:6]=4)[N:14]=3)[C:19]2=[N:30][N:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-4-hydrazino-6-oxo-6,7-dihydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-1-methyl-1H-pyrrole-3-carbonitrile (0.13 g) in dioxane (3 mL) was added cyanogen bromide (0.15 mL). The reaction was heated by microwave at 100° C. for 5 min. The mixture was concentrated and purified by HPLC yielding 27 mg of yellow foam, 1H NMR (300 MHz, CHLOROFORM-D) d ppm 0.56 (m, 4 H) 1.44 (m, 1H) 3.7 (s, 3H) 3.94 (m, 2H) 5.84 (m, 2H) 6.54 (d, 1H) 6.86 (m, 1H) 7.71 (m, 2H) 7.87 (m, 1H) 8.12 (m, 1H) 8.85 (m, 1H); ES M+H+=525.

Workup

concentrationThe mixture was concentrated
custompurified by HPLC

Sources & evidence

ORD record: ord-6ce6dad62ffb4393a637f93054587017
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371757B2

Reaction notes

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