Triethylamine → 6-Amino-N-(5-(2-cyclopropylvinyl)thiophen-2-ylmethyl)nicotinamide

HRID 2080215Notes

Reaction equation

HRID 2080215 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH:11]1([CH:14]=[CH:15][C:16]2[S:20][C:19]([CH2:21][NH2:22])=[CH:18][CH:17]=2)[CH2:13][CH2:12]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>CN(C)C=O.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:22][CH2:21][C:19]2[S:20][C:16]([CH:15]=[CH:14][CH:11]3[CH2:13][CH2:12]3)=[CH:17][CH:18]=2)=[O:8])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 67119557C-(5-(2-Cyclopropylvinyl)thiophen-2-yl)methylamine

Product 1

HCID 671196356-Amino-N-(5-(2-cyclopropylvinyl)thiophen-2-ylmethyl)nicotinamideYield 66.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-Aminonicotinic acid (35 mg, 0.251 mmol), C-(5-(2-cyclopropylvinyl)thiophen-2-yl)methylamine described in Preparation Example 151 (45 mg, 0.251 mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (133 mg, 0.301 mmol) and triethylamine (0.042 mL, 0.301 mmol) were dissolved in N,N-dimethylformamide (3 mL), and the solution was stirred at room temperature for 3 hours. Water (10 mL) was added to the reaction solution, which was then extracted with ethyl acetate (30 mL). The organic layer was washed, dried over anhydrous magnesium sulfate, then, the solvent was evaporated in vacuo, the obtained residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=3:1), and the title compound (50 mg, 0.167 mmol, 66.6%) was obtained as a white solid.

Workup

  1. extractionwas then extracted with ethyl acetate (30 mL)
  2. washThe organic layer was washed
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customthe obtained residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-7e48cadb1bcd4b22951a1201446d9ef8
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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