1-Hydroxybenzotriazole → HCID 67180248, compound

HRID 1863994

Reaction equation

HRID 1863994 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[CH2:14][NH:15][CH2:16][CH2:17][O:18][C:12]=3[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.[C:29]([O:33][C:34]([NH:36][CH2:37][C:38]1[CH:39]=[C:40]([CH:44]=[CH:45][CH:46]=1)[C:41](O)=[O:42])=[O:35])([CH3:32])([CH3:31])[CH3:30].Cl.C(N=C=NCCCN(C)C)C>C(#N)C.C(OCC)(=O)C.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]3[CH2:14][N:15]([C:41]([C:40]4[CH:39]=[C:38]([CH:46]=[CH:45][CH:44]=4)[CH2:37][NH:36][C:34](=[O:35])[O:33][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:42])[CH2:16][CH2:17][O:18][C:12]=3[N:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559293-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidHCID 690781546-(4-Fluorophenyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine

Product 1

HCID 67180248HCID 67180248, compoundYield 89.8%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(4-fluorophenyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.20 g) obtained in Reference Example 13C, 1-hydroxy-1H-benzotriazole (0.15 g), triethylamine (0.083 g) and 3-(tert-butoxycarbonylaminomethyl)benzoic acid (0.205 g) in acetonitrile (10 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.314 g), and the mixture was stirred at room temperature for 20 hrs. Ethyl acetate was added to the reaction mixture, and the mixture was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound (0.35 g) as a colorless amorphous powder.

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-43c476ba5ce64a4b9cf6588523737150
Source dataset
uspto-grants-2009_12
Patent number
US07625887B2

Linked notes

Loading…