Piconol → HCID 54172018, compound

HRID 974344Notes

Reaction equation

HRID 974344 reaction equation
C(OC(N=NC(OCC)=O)=O)C.[NH2:13][C:14]1[S:15][C:16]2[CH2:17][CH2:18][N:19]([CH2:24][CH:25]=[CH:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=3)[CH2:20][CH2:21][C:22]=2[N:23]=1.O[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:13][C:14]1[S:15][C:16]2[CH2:17][CH2:18][N:19]([CH2:24][CH:25]=[CH:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[CH:28]=3)[CH2:20][CH2:21][C:22]=2[N:23]=1

Participants

6

Reactant 4

HCID 11474PiconolHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 54375116HCID 54375116, compound

Product 1

HCID 54172018HCID 54172018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 57 mg (0.33 mmol) of diethyl-azodicarboxylate in 0.15 ml of anhydrous tetrahydrofuran is added dropwise, with stirring and cooling (internal temperature 0° C.), to 100 mg (0.33 mmol) of 2-amino-6-(3-(3-hydroxy-phenyl)allyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine and 36 mg (0.33 mmol) of 2-(hydroxymethyl)-pyridine and 86 mg (0.33 mmol) of triphenylphosphine in 1 ml of anhydrous tetrahydrofuran. After stirring overnight, whilst heating to ambient temperature, a further 0.33 mmol of triphenylphosphine and diethyl-azodicarboxylate are added at 0° C. and the mixture is stirred for another hour at ambient temperature. It is evaporated down in vacuo and distributed between ethyl acetate and water. The ethyl acetate phase is extracted with 2N hydrochloric acid. The aqueous hydrochloric acid phase is made alkaline with conc. ammonia and extracted with ethyl acetate; the organic phase is dried, filtered and evaporated down in vacuo. The evaporation residue is purified by column chromatography on silica gel (chloroform/methanol=5:1). Yield: 13 mg (10% of theory), Melting point: 35°-40° C. (foamy). Molecular peak (m/z): Calculated: 392 Found: 392

Workup

  1. stirringAfter stirring overnight
  2. temperaturewhilst heating to ambient temperature
  3. stirringthe mixture is stirred for another hour at ambient temperature
  4. customIt is evaporated down in vacuo
  5. extractionThe ethyl acetate phase is extracted with 2N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. customthe organic phase is dried
  8. filtrationfiltered
  9. customevaporated down in vacuo
  10. customThe evaporation residue is purified by column chromatography on silica gel (chloroform/methanol=5:1)

Sources & evidence

ORD record
ord-6005c56a56b14cd1acecd6c8edea514b
Source dataset
uspto-grants-1991_11
Patent number
US05068325

Reaction notes

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