Triethylamine → HCID 23130429, compound

HRID 2079968Notes

Reaction equation

HRID 2079968 reaction equation
[Li].[NH2:2][C:3]1[N:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.[O:15]([C:22]1[S:26][C:25]([CH2:27][NH2:28])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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>[NH2:2][C:3]1[N:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([NH:28][CH2:27][C:25]1[S:26][C:22]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:23][CH:24]=1)=[O:7]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27344352-amino-5-nitronicotinic acidHCID 3028194LithiumHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 23130515C-(5-Phenoxy thiophen-2-yl)methylamine

Product 1

HCID 23130429HCID 23130429, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Then, the resulting lithium salt of 2-amino-5-nitro-nicotinic acid, C-(5-phenoxy-thiophen-2-yl)-methylamine (60 mg, 0.29 mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (162 mg, 0.367 mmol) and triethylamine (103 μl, 0.735 mmol) were dissolved in N,N-dimethylformamide (2.0 mL), and the solution was stirred for 6 hours at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate, and the organic layer was washed with water and brine. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (87 mg, 0.24 mmol, 96%) was obtained as a pale yellow solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-318f5f89d8034bb6af286aee58aeef8e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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