Sodium Hydroxide → HCID 21072794, compound

HRID 1372889Notes

Reaction equation

HRID 1372889 reaction equation
COCCO[AlH2-]OCCOC.[Na+].CO[C:15](=O)[NH:16][C:17]1[CH:18]=[N:19][C:20]([N:31]2[CH2:36][CH2:35][S:34][CH2:33][CH2:32]2)=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[CH3:30].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:15][NH:16][C:17]1[CH:18]=[N:19][C:20]([N:31]2[CH2:32][CH2:33][S:34][CH2:35][CH2:36]2)=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[CH3:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 16684438Red-AlHCID 21072793(4-(4-Fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-carbamic acid methyl ester

Product 1

HCID 21072794HCID 21072794, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Methyl-[4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-amine can be produced by diluting Red-Al in toluene and adding this solution dropwise to a solution of [4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-carbamic acid methyl ester in toluene. The yellow solution obtained is stirred at room temperature, cooled to about 0° C., and poured slowly onto a mixture of 4 N aqueous sodium hydroxide and ice (very exothermic). After stirring, the phases are separated, the aqueous phase extracted with tert-butyl-methyl-ether, and the organic phases washed with brine. The combined organic extracts are dried and concentrated under reduced pressure to yield methyl-[4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-amine as a brown oil which can be used in the next step without further purification.

Workup

  1. customThe yellow solution obtained
  2. temperaturecooled to about 0° C.
  3. stirringAfter stirring
  4. customthe phases are separated
  5. extractionthe aqueous phase extracted with tert-butyl-methyl-ether
  6. washthe organic phases washed with brine
  7. customThe combined organic extracts are dried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6cd4ec774f8f4f2dbe6c1014d4f12ee6
Source dataset
uspto-grants-2007_01
Patent number
US07160881B2

Reaction notes

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