Triethylamine → Tert-butyl[(1r)-1-(2,5-difluorobenzyl)-2-(5,6-dihydro[1,2,4]triazolo[4,3-d][1,4]benzoxazepin-3-yl)ethyl]carbamate

HRID 1863962Notes

Reaction equation

HRID 1863962 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[F:33])[CH2:9][C:10]1[N:14]2[CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21](Cl)=[CH:20][C:19]=3[C:13]2=[N:12][N:11]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[H][H]>[Pd].CO>[C:1]([O:5][C:6](=[O:34])[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[F:33])[CH2:9][C:10]1[N:14]2[CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:13]2=[N:12][N:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 91178718Tert-butyl[(1r)-2-(10-chloro-5,6-dihydro[1,2,4]triazolo[4,3-d][1,4]benzoxazepin-3-yl)-1-(2,5-difluorobenzyl)ethyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 91364421Tert-butyl[(1r)-1-(2,5-difluorobenzyl)-2-(5,6-dihydro[1,2,4]triazolo[4,3-d][1,4]benzoxazepin-3-yl)ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 20 mg (0.0407 mmol) of tert-butyl[(1R)-2-(10-chloro-5,6-dihydro[1,2,4]triazolo[4,3-d][1,4]benzoxazepin-3-yl)-1-(2,5-difluorobenzyl)ethyl]carbamate, 0.007 mL (5.1 mg, 0.05 mmol) of triethylamine, 9.3 mg of 10% palladium on carbon, and 0.5 mL of methanol was shaken with hydrogen (45 psig) for 3 h. The catalyst was removed by filtration, and the filtrate was concentrated to yield the title compound. LC-MS 457 (M+1).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e1ef357d27ff4646a0ecdc44ff5415f9
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

Loading…