4-Aminopyridine → HCID 54518423, compound

HRID 363030Notes

Reaction equation

HRID 363030 reaction equation
C([C:3]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O)C.[NH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[CH2:21]1[O:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][O:12][C:10]3[CH:11]=[CH:3][C:4]([C:5]([NH:23][C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)=[O:7])=[CH:8][CH:9]=3)=[CH:15][C:16]=2[O:22]1

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 54223723HCID 54223723, compound

Product 1

HCID 54518423HCID 54518423, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 18-4 (0.545 g, 2 mmol) was added 4-aminopyridine 18-5 (0.235 g, 2.5 mmol), 1-hydroxy-benzotriazole hydrate (0.338 g, 2.5 mmol), 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide (0.479 g, 2.5 mmol) and dry DMF (5 ml) followed by triethylamine (0.35 ml, 2.5 mmol). The mixture was stirred at ambient temperature overnight. Then the DMF was removed under high vacuum. The residual oil was chromatographed on silica gel to obtain a white solid 18-6.

Workup

  1. customThen the DMF was removed under high vacuum
  2. customThe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-7b288af611a34b2f8670b694970106b5
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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