Acetic Acid → HCID 54206042, compound

HRID 1834368Notes

Reaction equation

HRID 1834368 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:9]([NH2:16])[C:8]([NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[N:7][C:6]=1[CH3:22])[CH3:2].C(O)(=O)C.[N:28]([O-])=O.[Na+]>O>[CH2:1]([O:3][C:4]([C:5]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:9]2[N:16]=[N:28][N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:8]2=[N:7][C:6]=1[CH3:22])=[O:23])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 53990871HCID 53990871, compound

Product 1

HCID 54206042HCID 54206042, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

33 g. of the oil obtained in part d, 5-amino-4-butylamino-6-(2-methylpropyl)amino-2-methylnicotinic acid ethyl ester (about 0.1 mol.), are dissolved in 100 ml. of acetic acid 20 ml. of water. A solution of 0.75 g. of sodium nitrite in 20 ml. of water is added dropwise at about 10° with stirring. Stirring is continued for 10 hours. After this time, the mixture is evaporated. The resulting oil is mixed with 100 ml. of water and extracted three times with 50 ml. portions of ether. The ether phase is dried over sodium sulfate, filtered and evaporated. The residue, 7-butylamino-5-methyl-3-(2-methylpropyl) [1,2,3]triazolo[4,5-b]pyridine-6-carboxylic acid ethyl ester, is recrystallized from benzene, yield 27 g. (81%), m.p. 34°-36°.

Workup

  1. customof the oil obtained in part
  2. stirringStirring
  3. customAfter this time, the mixture is evaporated
  4. additionThe resulting oil is mixed with 100 ml
  5. extractionof water and extracted three times with 50 ml
  6. dry with materialThe ether phase is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue, 7-butylamino-5-methyl-3-(2-methylpropyl) [1,2,3]triazolo[4,5-b]pyridine-6-carboxylic acid ethyl ester, is recrystallized from benzene, yield 27 g

Sources & evidence

ORD record
ord-850d51a46c5c430c957b1df7670177cb
Source dataset
uspto-grants-1978_01
Patent number
US04070362

Reaction notes

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