Dimethylformamide dimethyl acetal → (2E)-3-(dimethylamino)-1-{4-[1-(2-hydroxyethyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-12-yl}prop-2-en-1-one

HRID 1530653Notes

Reaction equation

HRID 1530653 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][CH:14]=[C:15]([C:23](=[O:25])[CH3:24])[CH:16]=2)=[N:7][CH:6]=[N:5]1.[CH3:26][N:27]([CH:29](OC)OC)[CH3:28]>>[CH3:26][N:27]([CH3:29])/[CH:28]=[CH:24]/[C:23]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[C:11]1[N:21]([CH:22]=[C:9]([C:8]3[N:4]([CH2:3][CH2:2][OH:1])[N:5]=[CH:6][N:7]=3)[N:10]=1)[CH2:20][CH2:19][O:18]2)=[O:25]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 683126921-{4-[1-(2-hydroxyethyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo [8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}ethan-1-one

Product 1

HCID 68312848(2E)-3-(dimethylamino)-1-{4-[1-(2-hydroxyethyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-12-yl}prop-2-en-1-oneYield 104.9%

Conditions

Temperature
130 °C

Procedure

A mixture of 1-{4-[1-(2-hydroxyethyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}ethan-1-one (115 mg, 0.290 mmol) and DMF-DMA (69 mg, 0.58 mmol) in xylenes (10 mL) was stirred at 130° C. for 48 h under nitrogen atmosphere. The mixture was then concentrated under reduced pressure, the residue was purified by reverse phase Combiflash eluting with a 0-40% gradient of CH3CN in 0.3% NH4HCO3 to give (2E)-3-(dimethylamino)-1-{4-[1-(2-hydroxyethyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}prop-2-en-1-one (120 mg, 90% yield). LCMS (ESI) m/z: 395.1 [M+H+].

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customthe residue was purified by reverse phase Combiflash
  3. washeluting with a 0-40% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record
ord-cb64e2a29e8b4aca804add75046ec427
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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