Dimethylformamide dimethyl acetal → HCID 178484340, compound

HRID 1530619Notes

Reaction equation

HRID 1530619 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]([NH2:18])=[O:17])[N:11]=1)[CH2:7][CH2:6][O:5]2.[CH3:19][N:20]([CH:22](OC)OC)[CH3:21]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16](/[N:18]=[CH:19]/[N:20]([CH3:22])[CH3:21])=[O:17])[N:11]=1)[CH2:7][CH2:6][O:5]2

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 582046299-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 178484340HCID 178484340, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 12-bromo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene-4-carboxamide (100 mg, 0.380 mmol) in 1,4-dioxane (3 mL) was added DMF-DMA (147 mg, 1.14 mmol). The resulting mixture was stirred at 100° C. for 1 h under nitrogen atmosphere. After removal of the solvent, the residue was washed with ether to afford 12-bromo-N-[(1E)-(dimethylamino)methylidene]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene-4-carboxamide (80 mg, 68% yield), which was used in the next step without further purification. LCMS (ESI) m/z: 363.3 [M+H+].

Workup

  1. customAfter removal of the solvent
  2. washthe residue was washed with ether

Sources & evidence

ORD record
ord-1ddeb9b91dfd42baac349090ddf5f719
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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