Pyridine → 5-Isopropoxycarbonylamino-2-phenyloxazolo[5,4-b]pyridine

HRID 259556Notes

Reaction equation

HRID 259556 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH:23]([O:26][C:27](Cl)=[O:28])([CH3:25])[CH3:24]>O>[CH:23]([O:26][C:27]([NH:1][C:2]1[N:7]=[C:6]2[O:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1)=[O:28])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 227547935-Amino-2-phenyloxazolo[5,4-b]pyridine

Product 1

HCID 227548035-Isopropoxycarbonylamino-2-phenyloxazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 300 mg. of 5-amino-2-phenyloxazolo[ 5,4-b]pyridine and 3 ml. of pyridine was cooled in ice and to it was added 0.2 ml. of isopropylchloroformate. The mixture was allowed to age in the refrigerator for 5 days, and diluted with ice and water. The precipitate was collected and recrystallized from isopropanol to give 5-isopropoxycarbonylamino-2-phenyloxazolo[ 5,4-b]pyridine, m.p. 210°-211° C.

Workup

  1. additionA mixture of 300 mg
  2. additionwas added 0.2 ml
  3. customThe precipitate was collected
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-08a2e0c4a7584ceda3507a0329221d89
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Reaction notes

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