Triethylamine → 2-aminochloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide
Reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[O:46]([C:53]1[S:57][C:56]([CH2:58][NH2:59])=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C)C=O.[Cl-].[Na+].O>[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:59][CH2:58][C:56]1[S:57][C:53]([O:46][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)=[CH:54][CH:55]=1)=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Amino-6-chloro-nicotinic acid described in Preparation Example A-1 (400 mg, 2.31 mmol) was dissolved in N,N-dimethylformamide (10 mL), triethylamine (0.78 mL, 5.6 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.23 g, 2.8 mmol) and C-(5-phenoxy-thiophen-2-yl)-methylamine described in Preparation Example 26 (572 mg, 2.8 mmol) were added, and the solution was stirred for 13 hours 30 minutes at room temperature. After the reaction was completed, the reaction solution was poured into brine, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), and the title compound (380 mg, 1.05 mmol, 46%) was obtained.
Workup
- additionwere added
- extractionwas then extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated
- customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)
Sources & evidence
- ORD record
- ord-689af230705a475e9e7295c055f62ec0
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932272B2
Reaction notes
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