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4-Methylmorpholine → n-(2-Aminophenyl)-5-(biphenyl-4-ylcarbonyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

HRID 2093057
Notes
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Reaction equation

HRID 2093057 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.CN1CCOCC1.[NH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[NH:51][C:52]([C:54]1[S:55][C:56]2[CH2:57][NH:58][CH2:59][CH2:60][C:61]=2[N:62]=1)=[O:53]>CN(C=O)C>[NH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[NH:51][C:52]([C:54]1[S:55][C:56]2[CH2:57][N:58]([C:7]([C:4]3[CH:3]=[CH:2][C:1]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:6][CH:5]=3)=[O:9])[CH2:59][CH2:60][C:61]=2[N:62]=1)=[O:53]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 58117006N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

Product 1

HCID 66865245
n-(2-Aminophenyl)-5-(biphenyl-4-ylcarbonyl)-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 a solution of biphenyl-4-carboxylic acid (1.0 mmol) in dry 10 mL DMF, 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 from step VIII of example 1 (1.1 mmole.) 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 chromatography to yield the title compound.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. additiondiluted with water
  4. extractionextracted with dichloromethane
  5. washwashed with brine solution
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationConcentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-50bf951b9f1b439b8af8161298520a62
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440830B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes