Dimethylformamide dimethyl acetal → (2E)-3-(dimethylamino)-1-{13-methyl-4-[1-(propan-2-yl)-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 1530665Notes

Reaction equation

HRID 1530665 reaction equation
[CH3:1][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]2[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=2)=[CH:10]3)=[CH:4][C:3]=1[C:24](=[O:26])[CH3:25].[CH3:27][N:28]([CH:30](OC)OC)[CH3:29]>>[CH3:27][N:28]([CH3:30])/[CH:29]=[CH:25]/[C:24]([C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:2]=1[CH3:1])[C:13]1[N:9]([CH:10]=[C:11]([C:16]3[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=3)[N:12]=1)[CH2:8][CH2:7][O:6]2)=[O:26]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 683129221-{13-methyl-4-[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-pentaen-12-yl}ethan-1-one

Product 1

HCID 68312917(2E)-3-(dimethylamino)-1-{13-methyl-4-[1-(propan-2-yl)-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 82%

Conditions

Temperature
130 °C

Procedure

A mixture of 1-{13-methyl-4-[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-pentaen-12-yl}ethan-1-one (250 mg, 0.720 mmol) and DMF-DMA (170 mg, 1.44 mmol) in xylenes (10 mL) was stirred at 130° C. for 48 h under nitrogen atmosphere. After concentration, the residue was purified by reverse phase combiflash eluting with a 0-40% gradient of CH3CN in 0.3% NH4HCO3 to afford (2E)-3-(dimethylamino)-1-{13-methyl-4-[1-(propan-2-yl)-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 (240 mg, 77% yield). LCMS (ESI) m/z: 407.3 [M+H+].

Workup

  1. concentrationAfter concentration
  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-e9effad640fe4e0cbf7c9cb596be1c11
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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