Dimethylformamide dimethyl acetal → HCID 68313052, compound

HRID 1530678Notes

Reaction equation

HRID 1530678 reaction equation
[CH3:1][O:2][CH:3]([CH3:27])[CH2:4][N:5]1[C:9]([C:10]2[N:11]=[C:12]3[N:22]([CH:23]=2)[CH2:21][CH2:20][O:19][C:18]2[C:13]3=[CH:14][CH:15]=[C:16]([C:24](=[O:26])[CH3:25])[CH:17]=2)=[N:8][CH:7]=[N:6]1.[CH3:28][N:29]([CH:31](OC)OC)[CH3:30]>>[CH3:28][N:29]([CH3:31])/[CH:30]=[CH:25]/[C:24]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:22]([CH:23]=[C:10]([C:9]3[N:5]([CH2:4][CH:3]([O:2][CH3:1])[CH3:27])[N:6]=[CH:7][N:8]=3)[N:11]=1)[CH2:21][CH2:20][O:19]2)=[O:26]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 68312923HCID 68312923, compound

Product 1

HCID 68313052HCID 68313052, compoundYield 90%

Conditions

Temperature
130 °C

Procedure

A mixture of 1-{4-[1-(2-methoxypropyl)-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 (163 mg, 0.44 mmol) and DMF-DMA (112 mg, 0.88 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-{4-[1-(2-methoxypropyl)-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: 422.1 [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-4a8ffe4b3c374405a9e511b5e1b3fadb
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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