Methanol → HCID 86759103, compound

HRID 395857Notes

Reaction equation

HRID 395857 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.[C:41](Cl)(=[O:43])[CH3:42].CO>C(Cl)Cl>[C:41]([NH:15][C:12]1[CH:11]=[C:10]([NH:16][C:17]([O:19][CH:20]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)=[O:18])[C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:34][CH:33]=2)=[CH:14][CH:13]=1)(=[O:43])[CH3:42]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 6367Acetyl chlorideHCID 69360635HCID 69360635, compound

Product 1

HCID 86759103HCID 86759103, compoundYield 76.6%

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 acetyl chloride (0.006 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:MeOR), affording 32 mg (76%) 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:MeOR)

Sources & evidence

ORD record
ord-8d0e5398607e485393ae71631ed4b1c9
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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