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Triethylamine → 6-amino-N-(5-(3-fluoro-phenoxy)-thiophen-2-yl)-methylnicotinamide

HRID 2079959
Notes
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Reaction equation

HRID 2079959 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][CH:25]=1)[O:15][C:16]1[S:20]C(CN)=C[CH:17]=1.F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:36]=2N=N1.C([N:54]([CH2:57][CH3:58])CC)C>CN(C)C=O.CO.C(OCC)(=O)C.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:54][C:57]2[S:20][C:16]([O:15][C:14]3[CH:23]=[CH:24][CH:25]=[C:12]([F:11])[CH:13]=3)=[CH:17][CH:58]=2)=[O:8])=[C:4]([CH3:36])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 23130606C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine

Product 1

HCID 231305756-amino-N-(5-(3-fluoro-phenoxy)-thiophen-2-yl)-methylnicotinamideYield 43.9%

Reagents, catalysts & solvents

4
HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 6-amino-nicotinic acid (270 mg, 2.0 mmol) and C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine (400 mg, 1.8 mmol) in N,N-dimethylformamide (10 mL) were added benzotriazole-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (870 mg, 2.0 mmol) and triethylamine (0.50 mL, 3.6 mmol), and the solution was stirred for 30 minutes at 60° C. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed twice with water. Silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out with NH silica gel column chromatography (ethyl acetate, then ethyl acetate:methanol=10:1), and 6-amino-N-(5-(3-fluoro-phenoxy)-thiophen-2-yl)-methylnicotinamide (270 mg, 0.79 mmol, 43.9%) was obtained.

Workup

  1. customwas then partitioned
  2. washthe organic layer was washed twice with water
  3. additionSilica gel was added to the organic layer
  4. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-c34d88ad764542a390acfddc6744389b
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932272B2

Reaction notes

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