Diisopropylethylamine → HCID 11856771, compound

HRID 2105880Notes

Reaction equation

HRID 2105880 reaction equation
N1(O[C:11]([N:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C@H:16]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[N:15]=[C:14]2[C:32]2[CH:37]=[C:36]([S:38](=[O:42])(=[O:41])[NH:39][CH3:40])[C:35]([Cl:43])=[CH:34][C:33]=2[O:44][CH2:45][CH3:46])=[O:12])C2C=CC=CC=2N=N1.[N:47]1([C:53](=[O:61])[CH2:54][N:55]2[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]2)[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([C@H:16]2[C@@H:17]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[N:13]([C:11]([N:58]3[CH2:59][CH2:60][N:55]([CH2:54][C:53]([N:47]4[CH2:48][CH2:49][O:50][CH2:51][CH2:52]4)=[O:61])[CH2:56][CH2:57]3)=[O:12])[C:14]([C:32]3[C:33]([O:44][CH2:45][CH3:46])=[CH:34][C:35]([Cl:43])=[C:36]([S:38]([NH:39][CH3:40])(=[O:41])=[O:42])[CH:37]=3)=[N:15]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1006221-(Morpholinocarbonylmethyl)piperazineHCID 57809249HCID 57809249, compound

Product 1

HCID 11856771HCID 11856771, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (4S,5R)-2-(4-chloro-2-ethoxy-5-methylsulfamoyl-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-imidazole-1-carboxylic acid benzotriazol-1-yl ester (9 mg, 0.0124 mmol) in 0.5 mL of dimethylformamide was added a solution of 1-morpholin-4-yl-2-piperazin-1-yl-ethanone (5.3 mg, 0.026 mmol) and diisopropylethylamine (4.53 uL). The resulting mixture was heated to 40° C. for 1 h. The solution was concentrated in vacuo then extracted from 1 mL of water with 1 mL of methylene chloride. The organic extract was applied to a 4 gram silica gel cartridge. The product was eluted using a gradient of methanol in methylene chloride to give 5-{(4S,5R)-4,5-bis-(4-chloro-phenyl)-1-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl]-4,5-dihydro-1H-imidazol-2-yl}-2-chloro-4-ethoxy-N-methyl-benzenesulfonamide (9.69 mg, 97%). LC-MS: 777.3 [(M+H)+].

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. extractionthen extracted from 1 mL of water with 1 mL of methylene chloride
  3. extractionThe organic extract
  4. washThe product was eluted

Sources & evidence

ORD record
ord-cdab1887caac4ffe8d9fed382a6a6583
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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