Dimethylformamide dimethyl acetal → HCID 178432611, compound

HRID 1530647Notes

Reaction equation

[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[N:8]=[C:9]3[N:19]([CH:20]=2)[CH2:18][CH2:17][O:16][C:15]2[C:10]3=[CH:11][CH:12]=[C:13]([C:21]([NH2:23])=[O:22])[CH:14]=2)[N:4]([CH:24]([CH3:26])[CH3:25])[N:3]=1.[CH3:27][N:28]([CH:30](OC)OC)[CH3:29]>O1CCOCC1>[CH3:27][N:28](/[CH:30]=[N:23]/[C:21]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9]1[N:19]([CH:20]=[C:7]([C:5]3[N:4]([CH:24]([CH3:26])[CH3:25])[N:3]=[C:2]([CH3:1])[N:6]=3)[N:8]=1)[CH2:18][CH2:17][O:16]2)=[O:22])[CH3:29]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene-12-carboxamide (200 mg, 0.568 mmol) in dioxane (20 mL) was added DMF-DMA (0.2 mL, 1.7 mmol). The reaction mixture was heated at 100° C. for 1 h. The solvent was removed under reduce pressure and the resultant residue was triturated with hot diethyl ether. The solid was collected by filtration, washed with diethyl ether, and dried in vacuo to afford N-[(1E)-(dimethylamino)methylidene]-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene-12-carboxamide (180 mg, 78% yield) as a brown solid. LCMS (ESI) m/z: 408.3 [M+H+].

Workup

customThe solvent was removed
customthe resultant residue was triturated with hot diethyl ether
filtrationThe solid was collected by filtration
washwashed with diethyl ether
customdried in vacuo

Sources & evidence

ORD record: ord-1ff9cbb97a31411aab509183883ea1c0
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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