4-Aminopyridine → HCID 9953954, compound

HRID 618815Notes

Reaction equation

HRID 618815 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([S:10]([N:13]([CH2:27][C:28](Cl)=[O:29])[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=2)[O:17][C:16]([CH3:26])([CH3:25])[CH2:15]1)(=[O:12])=[O:11])[CH3:9]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1.C(Cl)Cl>[CH2:8]([S:10]([N:13]([CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=2)[O:17][C:16]([CH3:25])([CH3:26])[CH2:15]1)[CH2:27][C:28]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)=[O:29])(=[O:11])=[O:12])[CH3:9]

Participants

6

Reactant 2

HCID 17274-AminopyridineHCID 21848668HCID 21848668, compound

Product 1

HCID 9953954HCID 9953954, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

141 mg of p-aminopyridine and a spatula tipful of DMAP dissolved in 6 ml of pyridine are treated with a solution of 655 mg of [ethanesulfonyl-(6-fluoro-2,2-dimethylchroman-4-yl)amino]acetyl chloride in 6 ml of methylene chloride. The mixture is stirred at RT for 4 h and then concentrated in vacuo. The product is partitioned between EA and water and the organic phase is washed with water. After removing the solvent in vacuo, 600 mg of the product are obtained as a colorless foam (m.p. 195° C.).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product is partitioned between EA and water
  3. washthe organic phase is washed with water
  4. customAfter removing the solvent in vacuo, 600 mg of the product

Sources & evidence

ORD record
ord-13ab7df365dc4a6bb44db03c2834fc9e
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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