Dichloromethane → HCID 86648862, compound

HRID 43982Notes

Reaction equation

HRID 43982 reaction equation
Cl[CH2:2]Cl.[Cl:4][C:5]1[N:6]=[C:7]([C:12]([NH:14][C@H:15]2[CH2:20][CH2:19][N:18]([C:21]3[S:22][C:23]([C:27](O)=[O:28])=[C:24]([CH3:26])[N:25]=3)[CH2:17][C@H:16]2[O:30][CH3:31])=[O:13])[NH:8][C:9]=1[CH2:10][CH3:11].CCN=C=NC[CH2:38][CH2:39][N:40]([CH3:42])[CH3:41].Cl.C1C=CC2N(O)N=[N:50][C:48]=2C=1>C(OCC)(=O)C.C(=O)(O)[O-].[Na+].CC(N(C)C)=O>[Cl:4][C:5]1[N:6]=[C:7]([C:12]([NH:14][C@H:15]2[CH2:20][CH2:19][N:18]([C:21]3[S:22][C:23]([C:27]([NH:50][CH2:48][CH2:42][N:40]([CH2:39][CH3:38])[CH2:41][CH3:2])=[O:28])=[C:24]([CH3:26])[N:25]=3)[CH2:17][C@H:16]2[O:30][CH3:31])=[O:13])[NH:8][C:9]=1[CH2:10][CH3:11]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86648856cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 86648862HCID 86648862, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Dichloromethane (0.75 mL) and DMA (0.75 mL) were added to N,N-diethylene-1,2-diamine (6 mg, 0.05 mmol). While the mixture was stirred, cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acid obtained in Example (14a) (20 mg, 0.05 mmol), WSC hydrochloride (30 mg, 0.15 mmol) and HOBT (10 mg, 0.08 mmol) were added, followed by stirring at room temperature for one day. The reaction solution was diluted with ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was solidified with diethyl ether and hexane to obtain 11 mg of the title compound as a white solid (44%).

Workup

  1. stirringby stirring at room temperature for one day
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7645f0568dfb4578b29aa4d8af46418d
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

Loading…