Ammonia → HCID 21906527, compound

HRID 1882995Notes

Reaction equation

HRID 1882995 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:25][C:26]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[O:27])=[C:13]([CH:24]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=1)=[O:15].C(N(CC)CC)C.Br[CH:42]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH3:43].N>CN(C)C=O.CO>[ClH:8].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:25][C:26]([CH:28]2[CH2:29][CH2:30][N:31]([CH:42]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH3:43])[CH2:32][CH2:33]2)=[O:27])=[C:13]([CH:24]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=1)=[O:15]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 11454(1-Bromoethyl)benzeneHCID 21906226HCID 21906226, compound

Product 1

HCID 21906527HCID 21906527, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-chloro-N-(5-chloropyridin-2-yl)-2-[(4-piperidinylcarbonyl)amino]benzamide trifluoroacetate (0.2 g, 0.39 mmol) and triethylamine (0.115 mL, 0.82 mmol) in N,N-dimethylformamide (5 mL) was added (1-bromoethyl)benzene (0.065 mL, 0.47 mmol). After stirring for 72 h at room temperature, the solution was passed through an SCX column (2 N ammonia in methanol) and concentrated in vacuo. The preparative RPHPLC (C18) purification procedure was elution with a linear gradient of 80/20 to 50/50 (0.01% HCl/acetonitrile) over 180 min. The product containing fractions were combined and lyophilized to give 0.091 g (44%) of the title compound as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe preparative RPHPLC (C18) purification procedure
  3. washelution with a linear gradient of 80/20 to 50/50 (0.01% HCl/acetonitrile) over 180 min
  4. additionThe product containing fractions

Sources & evidence

ORD record
ord-e7c2c2c770e34b42929833b6e4d43489
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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