Hydrochloric Acid → HCID 178437826, compound

HRID 43978

Reaction equation

HRID 43978 reaction equation
ClCCl.[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]4[N:31](CCC#N)[N:30]=[N:29][N:28]=4)=[C:24]([CH3:26])[N:25]=3)[CH2:17][C@H:16]2[O:36][CH3:37])=[O:13])[NH:8][C:9]=1[CH2:10][CH3:11].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.Cl>C(OCC)(=O)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]4[NH:28][N:29]=[N:30][N:31]=4)=[C:24]([CH3:26])[N:25]=3)[CH2:17][C@H:16]2[O:36][CH3:37])=[O:13])[NH:8][C:9]=1[CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 86648857cis(+/-)-4-Chloro-N-(1-{5-[1-(2-cyanoethyl)-1H-tetrazol-5-yl]-4-methyl-1,3-thiazol-2-yl}-3-methoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxylic acid amide

Product 1

HCID 178437826HCID 178437826, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dichloromethane (1.5 mL) was added to cis(±)-4-chloro-N-(1-{5-[1-(2-cyanoethyl)-1H-tetrazol-5-yl]-4-methyl-1,3-thiazol-2-yl}-3-methoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxylic acid amide obtained in Example (262a) (16 mg, 0.03 mmol). While the mixture was stirred, diazabicycloundecene (15 mg, 0.10 mmol) was added, followed by stirring at room temperature overnight. The reaction solution was diluted with ethyl acetate and water. The organic layer was neutralized with 1 N hydrochloric acid, 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 7 mg of the title compound as a white solid (47%).

Workup

  1. stirringby stirring at room temperature overnight
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc9c4079df484dc482f8129e44f699a8
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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