Dimethylformamide dimethyl acetal → HCID 178484341, compound

HRID 2044276Notes

Reaction equation

HRID 2044276 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[N:10]([CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1)[CH:9]=[C:8]([C:14]([NH2:16])=[O:15])[N:7]=3.[CH3:19][N:20]([CH:22](OC)OC)[CH3:21]>O1CCOCC1>[CH3:19][N:20]([CH3:22])/[CH:21]=[N:16]\[C:14]([C:8]1[N:7]=[C:6]2[N:10]([CH2:11][CH2:12][O:13][C:4]3[CH:3]=[C:2]([Br:1])[CH:18]=[CH:17][C:5]=32)[CH:9]=1)=[O:15]

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 178484341HCID 178484341, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 8-bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid amide (7.67 g, 24.9 mmol) in dioxane (150 mL) was added DMF-DMA (9.92 mL, 74.7 mmol) and the reaction mixture heated at 100° C. for 1 h. During the reaction the solids dissolved to give a brown solution. The reaction mixture was concentrated in vacuo and the solid residue triturated with diethyl ether (˜150 mL). The product was collected by filtration and dried in vacuo at 45° C. for 3 h to yield 8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid 1-dimethylamino-meth-(Z)-ylideneamide as a buff coloured solid (8.52 g, 94%). 1H NMR (400 MHz, d6-DMSO) 8.56 (1H, s), 8.34 (1H, d, J=8.6 Hz), 7.96 (1H, s), 7.32 (1H, dd, J=8.6, 2.0 Hz), 7.26 (1H, d, J=2.1 Hz), 4.51-4.46 (4H, m), 3.16 (3H, s), 3.08 (3H, s). 1H NMR showed product to contain 5% 8-iodo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid 1-dimethylamino-meth-(Z)-ylideneamide.

Workup

  1. customDuring the reaction the solids
  2. dissolutiondissolved
  3. customto give a brown solution
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe solid residue triturated with diethyl ether (˜150 mL)
  6. filtrationThe product was collected by filtration
  7. customdried in vacuo at 45° C. for 3 h

Sources & evidence

ORD record
ord-80820798781d4b84b578e0ab6c2ce03c
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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