4-Methylmorpholine → N-(2-aminophenyl)-5-(N-1,3-benzodioxol-5-ylglycyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

HRID 2093114Notes

Reaction equation

HRID 2093114 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][CH2:11][C:12]([OH:14])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.CN1CCOCC1.[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[NH:50][C:51]([C:53]1[S:54][C:55]2[CH2:56][NH:57][CH2:58][CH2:59][C:60]=2[N:61]=1)=[O:52]>CN(C=O)C>[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[NH:50][C:51]([C:53]1[S:54][C:55]2[CH2:56][N:57]([C:12](=[O:14])[CH2:11][NH:10][C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[CH2:58][CH2:59][C:60]=2[N:61]=1)=[O:52]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5229860(Benzo[1,3]dioxol-5-ylamino)-acetic acidHCID 58117006N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

Product 1

HCID 66865008N-(2-aminophenyl)-5-(N-1,3-benzodioxol-5-ylglycyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of (Benzo[1,3]dioxol-5-ylamino)-acetic acid. (1.0 mmol) in dry DMF (10 mL), were added 1-hydroxybenzotriazole (1.2 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (2 mmol) and N-methylmorpholine (2.0 mmol). Solution was cooled to 0° C. N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide. obtained in step VIII of Example 1 was then added and mixture was stirred at room temperature overnight. Reaction mixture was concentrated, diluted with water, extracted with dichloromethane, washed with brine solution, and dried over anhydrous Na2SO4. Concentrated and purified by column chromatograph to obtained the title compound.

Workup

  1. customobtained in step VIII of Example 1
  2. additionwas then added
  3. customReaction mixture
  4. concentrationwas concentrated
  5. additiondiluted with water
  6. extractionextracted with dichloromethane
  7. washwashed with brine solution
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationConcentrated
  10. custompurified by column chromatograph

Sources & evidence

ORD record
ord-0df47081156449d4bddab5f547be9926
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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