1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 89923259, compound

HRID 921901Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH2:8]O)=[CH:6][C:5]([C:10]#[N:11])=[CH:4][C:3]=1[NH:12][C:13]1[N:18]=[C:17]([NH:19][CH:20]2[CH2:22][CH2:21]2)[C:16]2=[N:23][CH:24]=[C:25]([C:26]#[N:27])[N:15]2[N:14]=1.C1(P([N:42]=[N+:43]=[N-:44])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>O1CCOCC1.CCOC(C)=O>[N:42]([CH2:8][C:7]1[C:2]([Cl:1])=[C:3]([NH:12][C:13]2[N:18]=[C:17]([NH:19][CH:20]3[CH2:22][CH2:21]3)[C:16]3=[N:23][CH:24]=[C:25]([C:26]#[N:27])[N:15]3[N:14]=2)[CH:4]=[C:5]([C:10]#[N:11])[CH:6]=1)=[N+:43]=[N-:44]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-((2-chloro-5-cyano-3-(hydroxymethyl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 402)(120 mg, 0.315 mmol), diphenylphosphoryl azide (0.102 mL, 0.473 mmol) and DBU (0.071 mL, 0.473 mmol) in dry dioxane (3 mL) was heated at 70° C. for 20 hr. It was diluted with EtOAc and washed with water. The aqueous phase was washed with EtOAc and the combined organic phases were washed with brine and dried with sodium sulfate. Removal of the solvents followed by radial silica gel chromatography eluting with DCM containing 0 to 3% MeOH afforded 2-((3-(azidomethyl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (80 mg) as a white solid.

Workup

washwashed with water
washThe aqueous phase was washed with EtOAc
washthe combined organic phases were washed with brine
dry with materialdried with sodium sulfate
customRemoval of the solvents
washeluting with DCM containing 0 to 3% MeOH

Sources & evidence

ORD record: ord-50248438ce3d41e983a5011049d067f2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273057B2

Reaction notes

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