Sodium hydride → HCID 86708678, compound

HRID 921784Notes

Reaction equation

[H-].[Na+].[CH3:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([OH:12])[CH2:6][C:5]1([CH3:14])[CH3:13].[C:15]([C:17]1[C:18]([F:40])=[CH:19][C:20](F)=[C:21]([NH:23][C:24]2[N:29]=[C:28]([NH:30][CH:31]3[CH2:33][CH2:32]3)[C:27]3=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:26]3[N:25]=2)[CH:22]=1)#[N:16]>CN(C=O)C>[NH3:4].[C:15]([C:17]1[C:18]([F:40])=[CH:19][C:20]([O:12][CH:7]2[CH2:8][C:9]([CH3:10])([CH3:11])[N:4]([CH3:3])[C:5]([CH3:14])([CH3:13])[CH2:6]2)=[C:21]([NH:23][C:24]2[N:29]=[C:28]([NH:30][CH:31]3[CH2:33][CH2:32]3)[C:27]3=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:26]3[N:25]=2)[CH:22]=1)#[N:16]

Participants

Conditions

Temperature: 55 °C

Procedure

NaH (60% in mineral oil, 18 mg, 0.45 mmol) added to a solution of 1,2,2,6,6-pentamethylpiperidin-4-ol (73 mg, 0.43 mmol) in dry DMF (1 mL) at room temperature. This was left stirring for 30 min and then solid 2-((5-cyano-2,4-difluorophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 414) (50 mg, 0.14 mmol) was added. The reaction was left stirring at room temperature for ¾ hr and then heated at 55° C. for 7 hr. It was quenched with sat. aq. NH4C solution (0.5 mL) and diluted with DCM. After washing with water (3×), the organic phase was dried with sodium sulfate. The solvent was removed and radial silica gel chromatography with DCM containing 0 to 3% MeOH and then 1 to 4% 2N NH3 in MeOH afforded the title compound (37 mg) as a glass.

Workup

waitThis was left
waitThe reaction was left
stirringstirring at room temperature for ¾ hr
customIt was quenched with sat. aq. NH4C solution (0.5 mL)
additiondiluted with DCM
washAfter washing with water (3×)
dry with materialthe organic phase was dried with sodium sulfate
customThe solvent was removed

Sources & evidence

ORD record: ord-be6376afbaf644d098ac736d0dd16f40
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273057B2

Reaction notes

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