Triethylamine → 3,4-Dichloro-N-({1-[4-hydroxy-4-(6-methoxy-pyridin-3-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-benzamide

HRID 2096165Notes

Reaction equation

HRID 2096165 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH:6]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][C:13]([OH:24])([C:16]3[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[CH2:12][CH2:11]2)[CH2:7]1)=[O:4].[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[Cl:35])[C:29](Cl)=[O:30].CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[Cl:35])[C:29]([NH:1][CH2:2][C:3](=[O:4])[NH:5][CH:6]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][C:13]([OH:24])([C:16]3[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[CH2:12][CH2:11]2)[CH2:7]1)=[O:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 516892Sodium BicarbonateHCID 593615572-amino-N-{1-[4-hydroxy-4-(6-methoxy-pyridin-3-yl)-cyclohexyl]-azetidin-3-yl}-acetamide

Product 1

HCID 462419443,4-Dichloro-N-({1-[4-hydroxy-4-(6-methoxy-pyridin-3-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution containing 2-amino-N-{1-[4-hydroxy-4-(6-methoxy-pyridin-3-yl)-cyclohexyl]-azetidin-3-yl}-acetamide, as prepared in Step D of Example 16, (60 mg, 0.13 mmol), 3,4-dichloro benzoyl chloride (Aldrich, 27 mg, 0.13 mmol) and Et3N (76 uL, 0.54 mmol) in DCM (4 mL) was stirred at room temperature for 1 hour followed by aqueous workup with sat NaHCO3 and DCM. The organic layer was dried (Na2SO4) and concentrated in vacuo followed by column chromatography purification (5% NH3 in MeOH mixed with EtOAc) resulting in the title compound as a white solid.

Workup

  1. dry with materialThe organic layer was dried (Na2SO4)
  2. concentrationconcentrated in vacuo
  3. customfollowed by column chromatography purification (5% NH3 in MeOH mixed with EtOAc)

Sources & evidence

ORD record
ord-a45d4c6b4f4540568c3d9f7c636197dd
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

Loading…