Ethyl isocyanate → HCID 89923215, compound

HRID 921913Notes

Reaction equation

[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH:10]([CH2:14][OH:15])[CH2:9]2)=[CH:6][C:5]([C:16]#[N:17])=[CH:4][C:3]=1[NH:18][C:19]1[N:24]=[C:23]([N:25]([CH:35]2[CH2:37][CH2:36]2)CC2C=CC(OC)=CC=2)[C:22]2=[N:38][CH:39]=[C:40]([C:41]#[N:42])[N:21]2[N:20]=1.[CH2:43]([N:45]=[C:46]=[O:47])[CH3:44]>O1CCCC1>[CH2:43]([NH:45][C:46](=[O:47])[O:15][CH2:14][CH:10]1[O:11][CH2:12][CH2:13][N:8]([C:7]2[CH:6]=[C:5]([C:16]#[N:17])[CH:4]=[C:3]([NH:18][C:19]3[N:24]=[C:23]([NH:25][CH:35]4[CH2:37][CH2:36]4)[C:22]4=[N:38][CH:39]=[C:40]([C:41]#[N:42])[N:21]4[N:20]=3)[C:2]=2[Cl:1])[CH2:9]1)[CH3:44]

Participants

Conditions

Temperature: 50 °C

Procedure

To a vial was charged with 2-((2-chloro-5-cyano-3-(2-(hydroxymethyl)morpholino)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 1) (30 mg, 0.051 mmol) in tetrahydrofuran (256 μl) was added ethyl isocyanate (4.86 μl, 0.061 mmol). The vial was capped and heated at 50° C. over the weekend. Reaction temperature was raised to 70° C. for 6 h to get full conversion. Solvent was removed in vacuo and the crude residue was taken forward as is.

Workup

customThe vial was capped
customReaction temperature
temperaturewas raised to 70° C. for 6 h
customto get full conversion
customSolvent was removed in vacuo

Sources & evidence

ORD record: ord-efb7d438c8bf4aa6bb0e5edcc0610850
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273057B2

Reaction notes

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