Water → 4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(3,6-dihydro-2H-pyran-4-yl)-1,3,5-triazin-2-yl)aniline

HRID 707156Notes

Reaction equation

HRID 707156 reaction equation
O.[O:2]1[CH2:7][CH:6]=[C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)[N:11]=[C:10]([N:23]3[CH:28]4[CH2:29][CH2:30][CH:24]3[CH2:25][O:26][CH2:27]4)[N:9]=2)[CH2:4][CH2:3]1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[CH:24]12[N:23]([C:10]3[N:9]=[C:8]([C:5]4[CH2:6][CH2:7][O:2][CH2:3][CH:4]=4)[N:13]=[C:12]([C:14]4[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=4)[N:11]=3)[CH:28]([CH2:29][CH2:30]1)[CH2:27][O:26][CH2:25]2

Participants

6

Reactant 2

HCID 962WaterHCID 670219658-(4-(3,6-dihydro-2H-pyran-4-yl)-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane

Product 1

HCID 670220624-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(3,6-dihydro-2H-pyran-4-yl)-1,3,5-triazin-2-yl)anilineYield 74%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of iron powder (0.071 g, 1.27 mmoles) in acetic acid (2 ml) was heated to 55° C. for 15 minutes. Water (2 ml) was then added and oil bath was turned off. A solution of 8-(4-(3,6-dihydro-2H-pyran-4-yl)-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane (0.100 g, 0.253 mmol) in ethyl acetate (2 ml) was then added to this warm solution over 5 minutes. The mixture was cooled to RT and allowed to stir for 16 hours. The mixture was extracted with ethyl acetate by decantation (4×) into a sep. funnel containing saturated aqueous sodium carbonate. The combined organic extracts were washed with water, brine, dried, and concentrated to provide 4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(3,6-dihydro-2H-pyran-4-yl)-1,3,5-triazin-2-yl)aniline (0.068 g, 74%), which was used in the next step without purification. (M+H) 366.4.

Workup

  1. customoil bath was turned off
  2. temperatureThe mixture was cooled to RT
  3. extractionThe mixture was extracted with ethyl acetate by decantation (4×) into a sep
  4. additionfunnel containing saturated aqueous sodium carbonate
  5. washThe combined organic extracts were washed with water, brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cc3fd3b4d20b49efae0dde0cd6c187ba
Source dataset
uspto-grants-2015_11
Patent number
US09174963B2

Reaction notes

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