1,4-Dioxane → 5-(4-Chloro-phenyl)-6-cyclobutoxy-pyridin-3-ylamine

HRID 1958194Notes

Reaction equation

HRID 1958194 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([O:21][CH:22]2[CH2:25][CH2:24][CH2:23]2)=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:13]=1)(C)(C)C.O1CCOCC1>Cl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[CH:13]=[C:8]([NH2:7])[CH:9]=[N:10][C:11]=2[O:21][CH:22]2[CH2:25][CH2:24][CH2:23]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 68071757[5-(4-Chloro-phenyl)-6-cyclobutoxy-pyridin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 672811445-(4-Chloro-phenyl)-6-cyclobutoxy-pyridin-3-ylamineYield 46.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

[5-(4-Chloro-phenyl)-6-cyclobutoxy-pyridin-3-yl]-carbamic acid tert-butyl ester (1.042 g, 2.78 mmol) was dissolved in 4M HCl in dioxane (10.4 ml, 41.7 mmol). The reaction mixture was a light yellow solution and was stirred at room temperature for 1 h. The mixture was partitioned between ethyl acetate and 1M Na2CO3 solution. The organic phases were combined, dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 100 g, 5% to 75% ethyl acetate in heptane) to give 0.358 g (46.9%) of the title compound as light red oil; LC-MS (UV peak area/ESI) 94.3%, 275.0950 (M+H)+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and 1M Na2CO3 solution
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography (silica gel, 100 g, 5% to 75% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-c846f2c4743045c18923962498ce0f75
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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