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 (400 mg, 2.31 mmol) described in Preparation Example A-1 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 (572 mg, 2.8 mmol) described in Preparation Example 35 were added thereto, 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, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the resulting 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
- extractionthe solution was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated
- customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)
Sources & evidence
- ORD record
- ord-b6738ebb7bde4393b04fa8b1984b44bf
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932272B2
Reaction notes
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