HCID 59395015, compound → HCID 59394952, compound

HRID 471936Notes

Reaction equation

HRID 471936 reaction equation
[C:1](=[O:25])([O:23][CH3:24])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([C:12]#[C:13][CH2:14][N:15]([CH3:17])[CH3:16])=[CH:5][C:4]=1[CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)(=O)C.O.CO.[Zn]>[C:1](=[O:25])([O:23][CH3:24])[O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([C:12]#[C:13][CH2:14][N:15]([CH3:17])[CH3:16])=[CH:5][C:4]=1[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 1

HCID 59395015HCID 59395015, compound

Product 1

HCID 59394952HCID 59394952, compoundYield 57.5%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Cyclopentyl-4-(3-(dimethylamino)prop-1-ynyl)-5-nitrophenyl methyl carbonate (800 mg, 2.31 mmol) was dissolved in a mixture of glacial acetic acid (10 mL) and water (2.5 mL). Zn dust (1511 mg, 23.10 mmol) was added at room temperature. The solution was stirred for 10 min then diluted with methanol (5 mL) and filtered. The solution was concentrated and redissolved in ethyl acetate. The ethyl acetate solution was washed with 50% saturated NaHCO3 (2×20 mL) and brine, dried over Na2SO4, filtered, and dried down to a light orange solid. Purification by silica gel chromatography (5-15% methanol/dichloromethane) provided 5-amino-2-cyclopentyl-4-(3-(dimethylamino)prop-1-ynyl)phenyl methyl carbonate as a light orange oil (420 mg, 57% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.07 (s, 1H), 6.47 (s, 1H), 5.31 (s, 2H), 3.83 (d, J=5.7 Hz, 3H), 3.48 (d, J=4.6 Hz, 2H), 2.86-2.81 (m, 1H), 2.23 (s, 6H), 1.87-1.80 (m, 2H), 1.74-1.66 (m, 2H), 1.62-1.55 (m, 2H), 1.45-1.38 (m, 2H).

Workup

  1. filtrationfiltered
  2. concentrationThe solution was concentrated
  3. dissolutionredissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed with 50% saturated NaHCO3 (2×20 mL) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customdried down to a light orange solid
  8. customPurification by silica gel chromatography (5-15% methanol/dichloromethane)

Sources & evidence

ORD record
ord-2092ca90128f4a12a43d580659c2b22d
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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