Ethyl orthoformate → HCID 68299284, compound

HRID 532499Notes

Reaction equation

HRID 532499 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]4[S:23][CH:22]=[C:21]([C:24]5[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=5)[C:17]=4[N:18]=[CH:19][N:20]=3)[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[CH2:31](OC(OCC)OCC)C.[N-:41]=[N+:42]=[N-:43].[Na+]>C(O)(=O)C>[N:30]1([C:27]2[CH:26]=[CH:25][C:24]([C:21]3[C:17]4[N:18]=[CH:19][N:20]=[C:15]([N:12]5[CH2:11][CH2:10][CH:9]([C:7]6[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=6)[CH2:14][CH2:13]5)[C:16]=4[S:23][CH:22]=3)=[CH:29][CH:28]=2)[CH:31]=[N:43][N:42]=[N:41]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 68299334HCID 68299334, compound

Product 1

HCID 68299284HCID 68299284, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

4-(4-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)thieno[3,2-d]pyrimidin-7-yl)benzenamine was dissolved in acetic acid, and triethylorthoformate and sodium azide were added thereto followed by stirring at 100° C. for 12 hr. When the reaction is terminated, the resulting mixture was distilled under a reduced pressure to remove acetic acid, and ethyl acetate was added thereto, followed by washing with satuated sodium bicarbonate and water. Subsequently, the resultant was dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure to obtain the title compound.

Workup

  1. customWhen the reaction is terminated
  2. distillationthe resulting mixture was distilled under a reduced pressure
  3. customto remove acetic acid, and ethyl acetate
  4. additionwas added
  5. washby washing with satuated sodium bicarbonate and water
  6. dry with materialSubsequently, the resultant was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-e91d8c81368b41c0801caa29dc54ac30
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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