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

HRID 2079959Notes

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

Participants

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

customwas then partitioned
washthe organic layer was washed twice with water
additionSilica gel was added to the organic layer
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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