Cyclopentylamine → HCID 1447952, compound

HRID 1259491Notes

Reaction equation

HRID 1259491 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH:11]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(N(CC)CC)C>C1COCC1>[CH:11]1([NH:16][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 2428196-Fluoronicotinic Acid

Product 1

HCID 1447952HCID 1447952, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

6-Fluoronicotinic acid (300 mg, 2.13 mmol) and cyclopentylamine (0.84 mL, 8.50 mmol) were combined in anhydrous THF (5 mL) and triethylamine (0.59 mL, 4.25 mmol). The mixture was heated at 60° C. for 3 days. The mixture was concentrated under reduced pressure, and the residue was suspended in water. The aqueous mixture was brought to pH 3 with phosphoric acid. The resulting precipitate was collected by vacuum filtration, washed with water, and dried in a vacuum oven for 1 h at 50° C. to give the title compound as a solid (63 mg, 14%): HPLC MS RT=1.14 min, MH+=207.2; 1H NMR (DMSO-d6) δ: 12.29 (1H, broad s), 8.50 (1H, d), 7.73 (1H, dd), 7.29 (1H, d), 6.42 (1H, d), 4.16 (1H, broad s), 1.90 (2H, m), 1.67 (2H, m), 1.53 (2H, m), 1.43 (2H, m).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. filtrationThe resulting precipitate was collected by vacuum filtration
  3. washwashed with water
  4. customdried in a vacuum oven for 1 h at 50° C.

Sources & evidence

ORD record
ord-0f07cf08fcd34efd8ae5c29526d96048
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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