HCID 59787348, compound → HCID 68857448, compound

HRID 1965973Notes

Reaction equation

HRID 1965973 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:23][N:22]([CH3:31])[N:21]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[C:20]1[C:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:23][N:22]([CH3:31])[N:21]=1

Participants

3

Reactant 1

HCID 59787348HCID 59787348, compound

Product 1

HCID 68857448HCID 68857448, compoundYield 177.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Stir 3-tert-butoxycarbonyl-7-chloro-6-(2-methyl-5-phenyl-2H-[1,2,3]triazol-4-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (7.8 mg, 18 μmol) in trifluoroacetic acid (2 mL) at room temperature for 5 h. Concentrate in vacuo and purify the residue by HPLC (Zorbax SB-Phenyl column, 21.2×250 mm; flow rate: 22 mL/min; eluting with 10 to 90% acetonitrile in 0.1% aqueous trifluoroacetic acid). Concentrate in vacuo and elute the residue through a SCX column. Use a method similar to the General Procedure 2-2 and evaporate by lyophylization to obtain the title compound (6 mg, 100%). MS (ES+) m/z: 339 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. custompurify the residue
  3. washby HPLC (Zorbax SB-Phenyl column, 21.2×250 mm; flow rate: 22 mL/min; eluting with 10 to 90% acetonitrile in 0.1% aqueous trifluoroacetic acid)
  4. concentrationConcentrate in vacuo
  5. washelute the residue through a SCX column
  6. customevaporate by lyophylization

Sources & evidence

ORD record
ord-55fb7b7dd3ca4a969fd0f12cde5e2d1a
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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