Ammonium formate → HCID 178420024, compound

HRID 1846806Notes

Reaction equation

HRID 1846806 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][C@H:14]3[CH2:19][CH2:18][C@H:17]([NH:20][C:21]4[S:22][C:23]5[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=5[N:25]=4)[CH2:16][CH2:15]3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:8]([O:13][C@H:14]3[CH2:15][CH2:16][C@H:17]([NH:20][C:21]4[S:22][C:23]5[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=5[N:25]=4)[CH2:18][CH2:19]3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178419853HCID 178419853, compound

Product 1

HCID 178420024HCID 178420024, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of N-(trans-4-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)cyclohexyl)benzo[d]thiazol-2-amine. As prepared in Example 30b, (0.22 g, 0.54 mmol), palladium hydroxide on carbon (20 wt % Pd dry basis, wet, Degussa type E101 NE/W) (0.60 g), and ammonium formate (0.51 g, 8.11 mmol) in methanol (3 mL) was heated to 65° C. for 12 h, then cooled to RT. The palladium was filtered off and the filtrate was concentrated in vacuo to give a white solid. This solid was partitioned between ethyl acetate and water, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil. The oil was then purified by silica gel chromatography to give N-(trans-4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)cyclohexyl)benzo[d]thiazol-2-amine (0.030 g, 0.073 mmol, 14% yield) as a white solid. [M+1] 411.2. IC50 (uM): 0.0635.

Workup

  1. temperaturecooled to RT
  2. filtrationThe palladium was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a white solid
  5. customThis solid was partitioned between ethyl acetate and water
  6. customthe layers were separated
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give an oil
  11. customThe oil was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-789e4e49f9d14b4f9886e7dc93f28af0
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

Loading…