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Chemical Structure| 86499-35-6

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Product Details of [ 86499-35-6 ]

CAS No. :86499-35-6
Formula : C10H12N2O
M.W : 176.22
SMILES Code : NC1CCC2=CC=CC=C2NC1=O
MDL No. :MFCD02258897
InChI Key :AUAKXRGQXZRTQC-UHFFFAOYSA-N
Pubchem ID :4434433

Safety of [ 86499-35-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 86499-35-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 86499-35-6 ]

[ 86499-35-6 ] Synthesis Path-Downstream   1~4

  • 1
  • 4,4-dimethyul-α-tetralone [ No CAS ]
  • [ 19832-98-5 ]
  • [ 529-34-0 ]
  • [ 86499-35-6 ]
YieldReaction ConditionsOperation in experiment
Step A Alkylation of 3-Amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one 3-Amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one was prepared from alpha-tetralone using the methods described in Armstrong et al. Tetrahedron Letters. 1994, 35, 3239. The following compounds were as prepared by this procedure for use in the following steps: 5-methyl-3-amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (from 4-methyl-alpha-tetralone (Aldrich)); and 5,5-dimethyl-3-amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (from 4,4-dimethyul-alpha-tetralone (Aldrich)).
  • 2
  • [ 248921-66-6 ]
  • [ 56602-33-6 ]
  • [ 86499-35-6 ]
  • [ 77-92-9 ]
  • [ 145486-02-8 ]
YieldReaction ConditionsOperation in experiment
480 mg (100%) With triethylamine; In dichloromethane; ethyl acetate; Step A: 2(R)-t-Butoxycarbonylamino-3-(t-butoxy)-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]propanamide To a solution of 200 mg (1.13 mmol) of 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Example 1, Step B) in 8 mL of dry methylene chloride was added 0.206 mL (1.48 mmol) of triethylamine, 553 mg (1.25 mmol) of <strong>[248921-66-6]BOC-D-serine t-butyl ether</strong> followed by 602 mg (1.36 mmol) of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate. The reaction mixture was stirred at room temperature for 2 hours then diluted with 100 mL of ethyl acetate, washed with 25 mL of 5% aqueous citric acid, 25 mL of saturated sodium bicarbonate and 25 mL of brine. The organic layer was dried over magnesium sulfate, filtered and the solvents removed under vacuum. The residue was purified by flash chromatography on silica gel, eluding with ethyl acetate/hexane (55:45) to afford 480 mg (100%) of the product as a white foam. 1 H NMR (200 MHz,CDCl3): 1.20 (s,9H), 1.47 (s,9H), 1.92 (m,1H), 2.55-3.02 (m,3H), 3.38 (t,8 Hz,1H), 3.78 (m,1H), 4.15 (m,1H), 4.52 (m,1H), 5.45 (s,1H), 7.00 (m,1H), 7.10-7.35 (m,3H), 7.68 (d,4 Hz,1H), 8.05 (s,1H). FAB-MS: calculated for C22 H33 N3 O5 419; found 420 (M+H,20%), 426 (M+Li,40%).
  • 3
  • [ 13734-31-1 ]
  • [ 86499-35-6 ]
  • tert-butyl methyl((R)-1-oxo-1-((R)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)propan-2-yl)carbamate [ No CAS ]
  • tert-butyl methyl((R)-1-oxo-1-((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)propan-2-yl)carbamate [ No CAS ]
  • 4
  • [ 13734-31-1 ]
  • [ 86499-35-6 ]
  • (R)-2-methylamino-N-((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)propionamide [ No CAS ]
  • (R)-2-methylamino-N-((R)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)propionamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.409 mg; 0.383 mg With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; for 1h; A solution ofHBTU (1.29 g, 3.4 mmol, Eq: 1.2) and HOBT?H20 (521 mg, 3.4 mmol, Eq:15 1.2) in DMF (10 mL) was added to a mixture of3-amino-1,3,4,5-tetrahydro-benzo[b]azepin-2-one(0.5 g, 2.84 mmol, Eq: 1.00), BOC-N-Me-D-Ala-OH (692 mg, 3.4 mmol, Eq: 1.2) and TEA (861mg, 1.19 mL, 8.51 mmol, Eq: 3) in DMF (10 mL). After 1 h the mixture was diluted with EtOAC,washed with brine, sat. NaHC03, brine, dried over Na2S04 and concentrated. The residue waspurified by flash chromatography to afford two diastereomers whose absolute stereochemistries20 were assigned based on the biological activities after conversion to the target compounds. Lesspolar Isomer: I-2-methylamino-N-((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)propionamide(0.409 g, white solid). More polar isomer: I-2-methylamino-N-(I-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)-propionamide (0.383 g, white solid).
 

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