Dichloromethane → HCID 86648862, compound

HRID 1425451Notes

Reaction equation

HRID 1425451 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-326b8ee37edc42d1972d7f2cacb202f8
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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