Pyridine → HCID 69489853, compound

HRID 1296758Notes

Reaction equation

HRID 1296758 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:25]=[C:24]([C:26]2[N:30]=[C:29]([CH3:31])[O:28][N:27]=2)[CH:23]=[CH:22][C:6]=1[CH2:7][NH:8][C:9](=[O:21])[C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([CH3:18])=[C:12]([O:19][CH3:20])[CH:11]=1.N1C=CC=CC=1.[C:38](Cl)(=[O:40])[CH3:39]>ClCCl>[C:38]([NH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:25]=[C:24]([C:26]2[N:30]=[C:29]([CH3:31])[O:28][N:27]=2)[CH:23]=[CH:22][C:6]=1[CH2:7][NH:8][C:9](=[O:21])[C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([CH3:18])=[C:12]([O:19][CH3:20])[CH:11]=1)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chloride2×HCID 69491452HCID 69491452, compound

Product 1

HCID 69489853HCID 69489853, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 44a (21 mg, 0.05 mmol) and pyridine (0.008 mL, 0.1 mmol) in dichloromethane (1 mL) was added acetyl chloride (0.004 mL, 0.055 mmol). The reaction mixture was stirred for 1.5 h, and additional acetyl chloride (0.004 mL) was added. After an additional 5 min, the reaction was quenched by addition of water and concentrated. The residue was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.1% TFA) to afford compound 45a (8 mg).

Workup

  1. waitAfter an additional 5 min
  2. customthe reaction was quenched by addition of water
  3. concentrationconcentrated
  4. customThe residue was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.1% TFA)

Sources & evidence

ORD record
ord-a1d15ece073646a1990ef05960e9be0b
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

Loading…