Sodium Bicarbonate → HCID 178508824, compound

HRID 449082Notes

Reaction equation

HRID 449082 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:19]3[C:14]([C:15]([NH2:20])=[N:16][CH:17]=[N:18]3)=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:23][CH:22]=3)[N:12]=2)[CH2:7][CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O-])(O)=O.[Na+]>C1COCC1>[NH2:20][C:15]1[C:14]2=[C:13]([C:21]3[CH:22]=[CH:23][C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:25][CH:26]=3)[N:12]=[C:11]([C@H:8]3[CH2:7][CH2:6][C@H:5]([CH2:3][OH:2])[CH2:10][CH2:9]3)[N:19]2[N:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 178501054HCID 178501054, compound

Product 1

HCID 178508824HCID 178508824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of trans-4-[4-amino-5-(4-phenoxy-phenyl)-imidazo[5,1-f][1,2,4]triazin-7-yl]-cyclohexanecarboxylic acid methyl ester (105.0 mg, 0.2368 mmol) in THF (7 mL) was added solution of LiAlH4 in THF (1.0 M, 1.0 mL) at −78° C. The solution was allowed to warm to rt. Sat. aq. NaHCO3 (10 mL) was added to the reaction mixture, and the THF was removed in vacuo. DCM was added, and the mixture was transferred to a separatory funnel. The organic layer was extracted with sat. aq. NaHCO3, washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo to afford the title compound as an off-white solid. MS (ES+): m/z 416.09 (100) [MH+]. HPLC tR=3.12 min (OpenLynx, polar—5 min).

Workup

  1. customthe THF was removed in vacuo
  2. additionDCM was added
  3. customthe mixture was transferred to a separatory funnel
  4. extractionThe organic layer was extracted with sat. aq. NaHCO3
  5. washwashed with brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c75988af8af4a139178fbf77b674a06
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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