Ethyl isocyanate → HCID 15171542, compound

HRID 728138Notes

Reaction equation

HRID 728138 reaction equation
CC1C=CN=C(C(NC(=O)CCC2C=CC(N)=C(O)C=2)C)C=1.C(N=C=O)C.[CH3:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([CH:35]([NH:37][C:38](=O)[CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([NH:47][C:48]([NH:50][CH2:51][CH3:52])=O)=[C:43]([OH:53])[CH:42]=2)[CH3:36])[CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:36][C:35]1[N:37]=[C:38]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]3[N:47]=[C:48]([NH:50][CH2:51][CH3:52])[O:53][C:43]=3[CH:42]=2)[N:32]2[CH:33]=[CH:34][C:29]([CH3:28])=[CH:30][C:31]=12

Participants

6

Reactant 4

HCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 15171489HCID 15171489, compoundHCID 15171537HCID 15171537, compound

Product 1

HCID 15171542HCID 15171542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methyl-2-[1-{3-(4-amino-3-hydroxyphenyl)propionamido}ethyl]pyridine (8.0 g) and ethyl isocyanate (2.2 ml) in tetrahydrofuran (100 ml) was stirred for 2.5 hours at ambient temperature. The solvent was evaporated in vacuo and the residue was dissolved with a mixture of methanol and chloroform (5:95 V/V) and washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to give a residue including 4-methyl-2-[1-[3-{4-(3-ethylureido)-3-hydroxyphenyl}propionamido]ethyl]pyridine. The residue was stirred with polyphosphate ester (66 g) at 140° C. for 1 hour. The mixture was poured into ice-water, adjusted to pH 8 with 20% potassium carbonate and extracted with tetrahydrofuran by salting out technique. The extract was washed with brine and dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was crystallized from a mixture of chloroform and ethyl acetate to give 6-[2-(1,7-dimethylimidazo[1,5-a]pyridin-3-yl)ethyl]-2-ethylaminobenzoxazole (1.7 g).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved with a mixture of methanol and chloroform (5:95 V/V)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customto give a residue
  7. extractionextracted with tetrahydrofuran
  8. washThe extract was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was crystallized from a mixture of chloroform and ethyl acetate

Sources & evidence

ORD record
ord-fe52347df388411485cdba97b8fc45b4
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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