Morpholine → tert-butyl 7-morpholino-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine-1-carboxylate

HRID 1618724Notes

Reaction equation

HRID 1618724 reaction equation
Cl[C:2]1[CH:18]=[N:17][C:5]2[S:6][CH2:7][CH2:8][N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:4]=2[CH:3]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+].[NH:59]1[CH2:64][CH2:63][O:62][CH2:61][CH2:60]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:62]1[CH2:63][CH2:64][N:59]([C:2]2[CH:18]=[N:17][C:5]3[S:6][CH2:7][CH2:8][N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:4]=3[CH:3]=2)[CH2:60][CH2:61]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 67285231tert-butyl 7-chloro-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine-1-carboxylate

Product 1

HCID 67284534tert-butyl 7-morpholino-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure N by using tert-butyl 7-chloro-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine-1-carboxylate (340 mg, 1.19 mmol), Pd2dba3 (109 mg, 0.119 mmol), XPhos (113 mg, 0.237 mmol), sodium ter-butoxide (228 mg, 2.371 mmol), morpholine (0.13 mL, 1.54 mmol) in toluene (8 mL) at 100° C. for 14 h. Purification by column chromatography (hexanes:EtOAc, 1:0 to 1:1) gave tert-butyl 7-morpholino-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine-1-carboxylate. Mass Spectrum (ESI) m/e=338.2 (M+1).

Workup

  1. customPrepared
  2. customat 100° C.
  3. customfor 14 h
  4. customPurification by column chromatography (hexanes:EtOAc, 1:0 to 1:1)

Sources & evidence

ORD record
ord-90f84912eab949ea8736de86e90fcbf1
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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