1,2-Dichloroethane → tert-Butyl (2-{2-[(4-{[(benzylamino)carbonyl]amino}benzyl)-amino]-2-oxoethyl}-1-oxo-2,3,4,5-tetrahydro-1H-2-benzazepin-5-yl)acetate

HRID 1179337Notes

Reaction equation

HRID 1179337 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[N:11]([CH2:20][C:21](O)=[O:22])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.C(Cl)CCl.[NH2:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([NH:46][C:47]([NH:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:48])=[CH:42][CH:41]=1>C(Cl)Cl.CN(C=O)C>[CH2:50]([NH:49][C:47]([NH:46][C:43]1[CH:42]=[CH:41][C:40]([CH2:39][NH:38][C:21](=[O:22])[CH2:20][N:11]2[CH2:10][CH2:9][CH:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:24])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]2=[O:19])=[CH:45][CH:44]=1)=[O:48])[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 21912577N-[4-(Aminomethyl)phenyl]-N'-benzylureaHCID 69434194[5-(2-tert-Butoxy-2-oxoethyl)-1-oxo-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl]acetic acid

Product 1

HCID 86591657tert-Butyl (2-{2-[(4-{[(benzylamino)carbonyl]amino}benzyl)-amino]-2-oxoethyl}-1-oxo-2,3,4,5-tetrahydro-1H-2-benzazepin-5-yl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

130 mg (0.39 mmol) of the acid 3 are dissolved in 30 ml of CH2Cl2 and 0.07 ml of HUnig base and 77 mg of EDC (0.4 mmol) are added at 0° C. After 1 h, 100 mg of amine 5 dissolved in 10 ml of DMF are added dropwise and the mixture is stirred for a further 1 h. It is stirred at room temp. for 16 h, the solution is then concentrated, the residue is taken up in CH2Cl2/water and the mixture is washed with 1% citric acid, 5% NaHCO3 solution and water. The organic phase is dried and concentrated (92 mg).

Workup

  1. additionare added dropwise
  2. stirringIt is stirred at room temp. for 16 h
  3. concentrationthe solution is then concentrated
  4. washthe mixture is washed with 1% citric acid, 5% NaHCO3 solution and water
  5. customThe organic phase is dried
  6. concentrationconcentrated (92 mg)

Sources & evidence

ORD record
ord-4dcd23db09d84b1ebc4a3cd05c6d3087
Source dataset
uspto-grants-2007_10
Patent number
US07279468B2

Reaction notes

Loading…