1-Aminocyclopentanemethanol → HCID 21877189, compound

HRID 724287Notes

Reaction equation

HRID 724287 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[N:22]=[CH:21][C:20]([F:23])=[CH:19][C:15]=1[C:16]([OH:18])=O.[NH2:24][C:25]1([CH2:30][OH:31])[CH2:29][CH2:28][CH2:27][CH2:26]1>ClCCl.CN(C)C1C=CN=CC=1>[Cl:13][C:14]1[N:22]=[CH:21][C:20]([F:23])=[CH:19][C:15]=1[C:16]([NH:24][C:25]1([CH2:30][OH:31])[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:18]

Participants

6

Reactant 3

HCID 663071-AminocyclopentanemethanolHCID 682631,1'-CarbonyldiimidazoleHCID 114352432-Chloro-5-fluoronicotinic acid

Product 1

HCID 21877189HCID 21877189, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Carbonyldiimidazole (254 mg, 1.57 mmol) was added to a suspension of 2-chloro-5-fluoro-nicotinic acid (250 mg, 1.42 mmol) in dichloromethane (10 ml) under nitrogen at room temperature. The resulting solution was stirred for 15 min after which a solution of (1-amino-cyclopentyl)-methanol (197 mg, 1.71 mmol) and 4-dimethylaminopyridine (9 mg, 0.07 mmol) in dichloromethane (5 ml) was added. The reaction was stirred at room temperature for 18 h then diluted with dichloromethane (20 mls) and washed with sat. ammonium chloride solution (20 ml). The organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The residue was triturated with dichloromethane (5 ml) to give 2-Chloro-5-fluoro-N-(1-hydroxymethyl-cyclopentyl)-nicotinamide (100 mg) as white solid.

Workup

  1. additionwas added
  2. washwashed with sat. ammonium chloride solution (20 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was triturated with dichloromethane (5 ml)

Sources & evidence

ORD record
ord-c38b93babbf24ec9b9c8edb9635fbf12
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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