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Sodium hydride → HCID 19369599, compound

HRID 849234
Notes
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Reaction equation

HRID 849234 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[C:11]([CH2:21][CH2:22][C:23]2[S:24][C:25]([CH2:29][CH3:30])=[C:26]([CH3:28])[N:27]=2)[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]=[C:42]([CH2:44]Cl)[CH:43]=1)[C:37]([O:39][CH3:40])=[O:38]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:9]1[CH:14]=[C:13]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[CH:12]=[C:11]([CH2:21][CH2:22][C:23]2[S:24][C:25]([CH2:29][CH3:30])=[C:26]([CH3:28])[N:27]=2)[N:10]=1)[CH2:44][C:42]1[CH:41]=[C:36]([C:37]([O:39][CH3:40])=[O:38])[CH:35]=[C:34]([Cl:33])[CH:43]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 19369740HCID 19369740, compoundHCID 19369759Methyl 3-chloro-5-(chloromethyl)benzoate

Product 1

HCID 19369599HCID 19369599, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×
HCID 8857
Ethyl Acetate
Solvent

Procedure

2-tert-butoxycarbonylamino-6-[2-(5-ethyl-4-methyl-1,3-thiazol-2-yl)ethyl]-4-morpholinopyridine (500 mg) obtained in Example 109-(1) was dissolved in dimethylformamide (12 ml), and 60% sodium hydride (58 mg) was added under cooling with ice, followed by stirring at room temperature for one hour. The reaction solution was cooled with ice, and a solution of methyl 3-chloro-5-chloromethylbenzoate (438 mg) in dimethylformamide (5 ml), was added thereto, followed by stirring at room temperature for 13 hours. The reaction solution was diluted with ethyl acetate, washed with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to obtain the above identified compound (628 mg).

Workup

  1. temperatureunder cooling with ice
  2. temperatureThe reaction solution was cooled with ice
  3. stirringby stirring at room temperature for 13 hours
  4. washwashed with water
  5. dry with materiala saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)
  8. customto obtain the

Sources & evidence

ORD record
ord-fd60ffbfbadc4d0bbb92b158e250d523
Source dataset
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06011039

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes