Methanol → HCID 86757565, compound

HRID 395856Notes

Reaction equation

HRID 395856 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-863c0af3bf954472ae80cca426e471df
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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