Pyridine → HCID 10238719, compound

HRID 1168162Notes

Reaction equation

HRID 1168162 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13](=[O:22])[C:14]3[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=3)[S:11][C:7]=2[C:6]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH3:35][O:36][CH2:37][C:38](Cl)=[O:39].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:35][O:36][CH2:37][C:38]([NH:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C:10]2[S:11][C:7]3[C:6]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)=[O:22])=[CH:15][CH:16]=1)=[O:39]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 96623Methoxyacetyl chlorideHCID 11280971HCID 11280971, compound

Product 1

HCID 10238719HCID 10238719, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4-aminometyl-benzamide (100 mg, 0.24 mmol), dissolved in dichloromethane (5 ml) is treated with pyridine (29 μl, 0.36 mmol) and methoxy-acetyl chloride (24 μl, 0.32 mmol) and stirred at ambient temperature for 15 h. Saturated aqueous sodium carbonate (6 ml) is added, the phases are separated and the aqueous solution extracted twice with each 5 ml dichloromethane. The combined organic phases are dryed over sodium sulphate, filtered and evaporated to dryness. Flash chromatography (silica, eluent: dichloromethane containing 3% methanol) afforded the title compound as white crystals (71% yield). MS: m/e=471(M+H+).

Workup

  1. customthe phases are separated
  2. extractionthe aqueous solution extracted twice with each 5 ml dichloromethane
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-0cb4ece8a47d49cc93873ee6758ca21a
Source dataset
uspto-grants-2003_09
Patent number
US06624163B2

Reaction notes

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