Tert-butyl {1-[5-chloro-3-(5-fluoropyridin-3-yl)-2-methoxy-4-methylphenyl]propyl}carbamate → 1-[5-Chloro-3-(5-fluoropyridin-3-yl)-2-methoxy-4-methylphenyl]propan-1-amine

HRID 510986Notes

Reaction equation

HRID 510986 reaction equation
[Cl:1][C:2]1[C:3]([CH3:28])=[C:4]([C:21]2[CH:22]=[N:23][CH:24]=[C:25]([F:27])[CH:26]=2)[C:5]([O:19][CH3:20])=[C:6]([CH:8]([NH:11]C(=O)OC(C)(C)C)[CH2:9][CH3:10])[CH:7]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[C:3]([CH3:28])=[C:4]([C:21]2[CH:22]=[N:23][CH:24]=[C:25]([F:27])[CH:26]=2)[C:5]([O:19][CH3:20])=[C:6]([CH:8]([NH2:11])[CH2:9][CH3:10])[CH:7]=1

Participants

4

Reactant 1

HCID 86666900Tert-butyl {1-[5-chloro-3-(5-fluoropyridin-3-yl)-2-methoxy-4-methylphenyl]propyl}carbamate

Product 1

HCID 866669031-[5-Chloro-3-(5-fluoropyridin-3-yl)-2-methoxy-4-methylphenyl]propan-1-amineYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The tert-butyl {1-[5-chloro-3-(5-fluoropyridin-3-yl)-2-methoxy-4-methylphenyl]propyl}carbamate (0.05 g, 0.12 mmol) was diluted with 4 M HCl in dioxane (4 mL) and was stirred at room temperature for 1 hour. The reaction was complete and the reaction mixture was concentrated to give 1-[5-chloro-3-(5-fluoropyridin-3-yl)-2-methoxy-4-methylphenyl]propan-1-amine as a semi-solid (100%). LCMS calculated for C16H16ClFNO (M+H)+: m/z=292.0. found: 292.0.

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-9218c43fcc23481d85ab2d5ef42cec12
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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