4-Nitrophenyl chloroformate → (6-Cyclopentyloxy-pyridin-3-yl)-carbamic acid 4-nitro-phenyl ester

HRID 657247Notes

Reaction equation

HRID 657247 reaction equation
[CH:1]1([O:6][C:7]2[N:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:16]>C1COCC1>[N+:24]([C:21]1[CH:20]=[CH:19][C:18]([O:17][C:15](=[O:16])[NH:13][C:10]2[CH:11]=[N:12][C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:8][CH:9]=2)=[CH:23][CH:22]=1)([O-:26])=[O:25]

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 167909726-(Cyclopentyloxy)pyridin-3-amine

Product 1

HCID 58770029(6-Cyclopentyloxy-pyridin-3-yl)-carbamic acid 4-nitro-phenyl esterYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-cyclopentyloxy-pyridin-3-ylamine (0.248 g, 1.39 mmol) in THF (2 mL) was added 4-nitrophenyl chloroformate (0.280 g, 1.39 mmol) portionwise. After stirring at rt for 1 h, a heavy precipitate formed in the organic layer. Filtration of the organic layer provided the title compound as a light pink solid (0.368 g, 77%). 1H-NMR (400 MHz, CDCl3): δ 11.1 (s, 1H), 9.11 (s, 1H), 9.04 (d, 1H), 8.26 (d, 2H), 7.40 (d, 2H), 7.14 (d, 1H), 5.36 (m, 1H), 2.11 (m, 2H), 1.97 (m, 2H), 1.84 (m, 2H), 1.71 (m, 2H).

Workup

  1. customa heavy precipitate formed in the organic layer
  2. filtrationFiltration of the organic layer

Sources & evidence

ORD record
ord-81f29183abf74d4f8b78f7e8776a6d9b
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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