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Triethylamine → (3-(4-Methoxy-phenyl)propionyl-amino)-6-(3-(3-pyridyl)allyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine

HRID 974333
Notes
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Reaction equation

HRID 974333 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([CH2:12][CH:13]=[CH:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:8][CH2:9][C:10]=2[N:11]=1.C(N(CC)CC)C.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38](Cl)=[O:39])=[CH:32][CH:31]=1>C(Cl)(Cl)Cl>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38]([NH:1][C:2]2[S:3][C:4]3[CH2:5][CH2:6][N:7]([CH2:12][CH:13]=[CH:14][C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH2:8][CH2:9][C:10]=3[N:11]=2)=[O:39])=[CH:32][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109324413-(4-Methoxyphenyl)propionyl chlorideHCID 543192542-Amino-6-(3-(3-pyridyl)allyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepin

Product 1

HCID 53917232(3-(4-Methoxy-phenyl)propionyl-amino)-6-(3-(3-pyridyl)allyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent
2×

Procedure

To a stirred mixture of 1.0 g (3.5 mmol) of 2-amino-6-(3-(3-pyridyl)allyl)-4,5,7,8-tetrahydro-6H- thiazolo[5,4-d]azepine and 0.53 ml (3.8 mmol) of triethylamine in 40 ml of anhydrous chloroform, there is added dropwise at ambient temperature a solution of 3- (4-methoxy-phenyl)-propionyl chloride (bp: 150° C./15 torr) in 7 ml of chloroform. The mixture is stirred for 3 hours at 60°-70° C., cooled and extracted with water. The dried and filtered chloroform solution is evaporated down in vacuo and the evaporation residue is purified by column chromatography on silica gel (chloroform/methanol=5:1). Yield: 0.74 g (47% of theory), Melting point: 168°-170° C. (ether).

Workup

  1. temperaturecooled
  2. extractionextracted with water
  3. customThe dried
  4. filtrationfiltered chloroform solution
  5. customis evaporated down in vacuo
  6. customthe evaporation residue is purified by column chromatography on silica gel (chloroform/methanol=5:1)

Sources & evidence

ORD record
ord-f1966946c99d4787a99f59d462f80082
Source dataset
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05068325

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes