Methanol → HCID 86757565, compound

HRID 427706Notes

Reaction equation

HRID 427706 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([NH:8][C:9]2[C:10]([NH:16][C:17]([O:19][CH:20]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[O:18])=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:41][S:42](Cl)(=[O:44])=[O:43].CO>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[C:10]([NH:16][C:17]([O:19][CH:20]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)=[O:18])=[CH:11][C:12]([NH:15][S:42]([CH3:41])(=[O:44])=[O:43])=[CH:13][CH:14]=2)=[O:7])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 69360635HCID 69360635, compound

Product 1

HCID 86757565HCID 86757565, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N1-(4-chlorobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2,4-benzenetriamine (40 mg, 0.08 mmol) in 5 mL of CH2Cl2 was treated with pyridine (1 mL) and methanesulfonyl chloride (0.008 mL, 0.09 mmol). After 16 h, the mixture was treated with MeOH (1 mL) and then concentrated. The residue was partitioned between EtOAc and NaOH (aq). The organic layer was dried (MgSO4), concentrated, and purified by chromatography (17:3 CH2Cl2:MeOH) affording 20 mg (40%) of the title compound.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between EtOAc and NaOH (aq)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by chromatography (17:3 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-be7faa4fabb54d7eb62e341c71fe7684
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

Loading…