Dimethylformamide → HCID 59398291, compound

HRID 39988Notes

Reaction equation

HRID 39988 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=[O:4].[Cl:6][C:7]1[C:16]([CH2:17][N:18]([CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][N:34]3[C:43]4[C:38](=[CH:39][CH:40]=[C:41]([O:44][CH3:45])[CH:42]=4)[N:37]=[CH:36][C:35]3=[O:46])[CH2:28][CH2:27]2)[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:15]C2NC(=O)[CH2:11][S:10][C:9]=2[CH:8]=1.[H-].[Na+].CI>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[Cl:6][C:7]1[C:16]([CH2:17][N:18]([CH:26]2[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][N:34]3[C:43]4[C:38](=[CH:39][CH:40]=[C:41]([O:44][CH3:45])[CH:42]=4)[N:37]=[CH:36][C:35]3=[O:46])[CH2:30][CH2:31]2)[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:15][C:1]2[N:2]([CH3:5])[C:3](=[O:4])[CH2:11][S:10][C:9]=2[CH:8]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59397895HCID 59397895, compound

Product 1

HCID 59398291HCID 59398291, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 20 mL of an N,N-dimethylformamide solution containing 0.57 g of tert-butyl (7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-ylmethyl)(1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 0.04 g of 60% sodium hydride was added, and stirred at room temperature for 1 hour. 0.24 g of methyl iodide was added, and stirred at room temperature for 2 hours. To the reaction mixture, water, ethyl acetate and toluene were added. The organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform:methanol=30:1] to give 0.23 g of tert-butyl (7-chloro-4-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-ylmethyl)(1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a pale brown foam.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 2 hours
  3. customThe organic layer was separated
  4. washwashed with aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform:methanol=30:1]

Sources & evidence

ORD record
ord-9e10eb0f104149f4988263c872399641
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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