4-Aminopyridine → HCID 86595791, compound

HRID 585510Notes

Reaction equation

HRID 585510 reaction equation
Br[CH2:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[NH:19][C:20]([C:22]3[S:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[O:21])[C:10]2=[O:28])=[CH:5][CH:4]=1.N[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1>ClCCCl.ClCCl.CO>[Cl:27][C:24]1[S:23][C:22]([C:20]([NH:19][C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]=2[C:17](=[O:18])[N:9]([CH2:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][NH:19][C:15]4[CH:16]=[CH:11][C:12]([C:36]5[CH:37]=[CH:32][CH:33]=[CH:34][N:35]=5)=[CH:13][CH:14]=4)=[CH:30][CH:29]=2)[C:10]3=[O:28])=[O:21])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 17274-AminopyridineHCID 22337024HCID 22337024, compound

Product 1

HCID 86595791HCID 86595791, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

50 mg (0.1 mmol) of N-{2-[4-(bromomethyl)phenethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-5-chloro-2-thiophenecarboxamide are introduced a little at a time into a solution of 37.4 mg (0.4 mmol) of 4-aminopyridine in 4 ml 1,2-dichloroethane. The mixture is stirred at room temperature overnight and then diluted with dichloromethane/methanol (98:2), washed with sat. sodium bicarbonate solution, dried over magnesium sulfate and concentrated. The residue is crystallized using dichloromethane/ether and the solid is filtered off with suction and dried under high vacuum. Yield: 25.1 mg (37.2% of theory); MS (ESI): m/z (%)=517 (M+H, 100);); LC-MS (Method 7): rt (%)=3.42 (77).

Workup

  1. washwashed with sat. sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is crystallized
  5. filtrationthe solid is filtered off with suction
  6. customdried under high vacuum
  7. customrt (%)=3.42 (77)

Sources & evidence

ORD record
ord-3b0c1f4b43994efb853f9371b108eac4
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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