Dimethylformamide dimethyl acetal → HCID 178484339, compound

HRID 1530533Notes

Reaction equation

HRID 1530533 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:16]([NH2:18])=[O:17])=[CH:10]3)=[CH:4][CH:3]=1.[CH3:19][N:20]([CH:22](OC)OC)[CH3:21]>O1CCOCC1>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:16](/[N:18]=[CH:19]/[N:20]([CH3:22])[CH3:21])=[O:17])=[CH:10]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 6831288310-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 178484339HCID 178484339, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 13-bromo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene-4-carboxamide (2.0 g, 6.5 mmol) in dioxane (30 mL) was added DMF-DMA (2.6 mL, 19 mmol). The reaction mixture was heated at 100° C. for 1 h. The solvent was removed under reduce pressure and the residue was triturated with hot diethyl ether. The solid was collected by filtration, washed with diethyl ether and dried in vacuo to afford 13-Bromo-N-[(1E)-(dimethylamino)methylidene]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene-4-carboxamide (2.2 g, 93% yield) as a yellow solid. LCMS (ESI) m/z: 365.1 [M+H+]

Workup

  1. customThe solvent was removed
  2. customthe residue was triturated with hot diethyl ether
  3. filtrationThe solid was collected by filtration
  4. washwashed with diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-71dd046e9a6b4e2fac1c8a1d1ad6f853
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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