Triethylamine → 2-Amino-N-(5-(4-chloro-phenoxy)-thiophen-2-ylmethyl)-nicotinamide

HRID 2080190Notes

Reaction equation

HRID 2080190 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[Cl:11][C:12]1[CH:25]=[CH:24][C:15]([O:16][C:17]2[S:21][C:20]([CH2:22][NH2:23])=[CH:19][CH:18]=2)=[CH:14][CH:13]=1.F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CS(C)=O.C(#N)C.O.FC(F)(F)C(O)=O>[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:23][CH2:22][C:20]1[S:21][C:17]([O:16][C:15]2[CH:24]=[CH:25][C:12]([Cl:11])=[CH:13][CH:14]=2)=[CH:18][CH:19]=1)=[O:6]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 729302-Aminonicotinic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 23130383C-(5-(4-chloro-phenoxy)-thiophen-2-yl)-methylamine

Product 1

HCID 231306912-Amino-N-(5-(4-chloro-phenoxy)-thiophen-2-ylmethyl)-nicotinamideYield 24.9%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6422Trifluoroacetic acidSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of 2-amino-nicotinic acid (21 mg, 0.15 mmol), C-(5-(4-chloro-phenoxy)-thiophen-2-yl)-methylamine described in Preparation Example 157 (36 mg, 0.15 mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (86 mg, 0.195 mmol) and triethylamine (0.065 mL, 0.45 mmol) in dimethylsulfoxide (1 mL) was stirred under nitrogen atmosphere for 17 hours at room temperature. This reaction solution was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and trifluoroacetic acid salt of the title compound (17.7 mg, 0.037 mmol, 24.9%) was obtained as a pale yellow solid.

Sources & evidence

ORD record
ord-83f7496b09fc48f5ae03c07e2e50694f
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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