Methylamine → HCID 69849271, compound

HRID 352232Notes

Reaction equation

HRID 352232 reaction equation
[C:1]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([N:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([C:27](O)=[O:28])[C:21]=3[C:20]3=[N:30][O:31][C:32]([CH3:33])=[C:19]3[C:18]2=[O:34])[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:39][NH2:40]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.ClCCl>[CH3:39][NH:40][C:27]([C:22]1[C:21]2[C:20]3[C:19](=[C:32]([CH3:33])[O:31][N:30]=3)[C:18](=[O:34])[N:17]([CH:13]3[CH2:14][CH2:15][CH2:16][CH:11]([CH2:10][NH:9][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:12]3)[C:26]=2[CH:25]=[CH:24][CH:23]=1)=[O:28]

Participants

7

Reactant 3

HCID 6329MethylamineHCID 24386Thionyl ChlorideHCID 22714071HCID 22714071, compound

Product 1

HCID 69849271HCID 69849271, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 598 (0.05 g, 0.11 mmol) in toluene (1.5 ml) under N2 was added thionyl chloride (0.5 ml) and heated at reflux for 3 h. The solution was concentrated using toluene to azeotrope. The residue was dissolved in dichloromethane (2 ml) under N2 and added methylamine (0.55 ml, 1.1 mmol) and DMAP (0.025 g, 0.22 mmol). The reaction was stirred overnight, diluted with dichloromethane, washed (0.1 N HCl, H2O, and brine), dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, acetone/CH2Cl2 gradient) gave the title compound (0.029 g, 56%). MS(ES+) (m/z) 473.2 [M+1].

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. concentrationThe solution was concentrated
  4. dissolutionThe residue was dissolved in dichloromethane (2 ml) under N2
  5. washwashed (0.1 N HCl, H2O, and brine)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-69cc7f90261d4986a858d6bfbf888072
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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