Triethylamine → HCID 23130508, compound

HRID 2080180Notes

Reaction equation

HRID 2080180 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.F[P-](F)(F)(F)(F)F.N1(O[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.C(OCC)(=O)C>[NH2:1][C:2]1[N:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH:27][CH2:26][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)=[CH:29][CH:28]=1)=[O:6]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 16771797HCID 16771797, compoundHCID 231304372-Amino-6-methoxymethylnicotinic acid

Product 1

HCID 23130508HCID 23130508, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-6-methoxymethyl-nicotinic acid described in Preparation Example A-11 (100 mg, 0.55 mmol) and 4-(pyridin-2-ylmethoxy)-benzylamine described in Preparation Example 171 (170 mg, 0.82 mmol) in N,N-dimethylformamide (5 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (290 mg, 0.66 mmol) and triethylamine (0.23 mL, 1.7 mmol), and the solution was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction solution for extraction, the organic layer was washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:2), and the title compound (150 mg, 0.40 mmol, 73%) was obtained as a colorless solid.

Workup

  1. washthe organic layer was washed with brine
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-0d844c0f4c13485b97396edd03ffe48b
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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