Sodium Bicarbonate → HCID 178508477, compound

HRID 449059Notes

Reaction equation

HRID 449059 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([NH2:20])[C:14]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:19]1[C:14]2[N:15]([C:11]([C@H:8]3[CH2:7][CH2:6][C@H:5]([CH2:3][OH:2])[CH2:10][CH2:9]3)=[N:12][C:13]=2[C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:25][CH:26]=2)[CH:16]=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 178501053HCID 178501053, compound

Product 1

HCID 178508477HCID 178508477, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trans-4-[8-amino-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexanecarboxylic acid methyl ester (150.0 mg, 0.3390 mmol) in THF (10 mL, 0.1 mol) was cooled to −78° C., and 1.0 M of LiAlH4 in THF (1.50 mL) was added dropwise. The solution was allowed to warm to rt. Sat. NaHCO3 (10 mL) was added to quench, 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. NaHCO3, washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo to afford the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3): δ=1.15-1.27 (m, 2H), 1.65-1.70 (m, 1H), 1.84-1.96 (m, 2H), 1.98-2.05 (m, 2H), 2.10-2.16 (m, 2H), 2.87-2.97 (m, 1H), 3.56 (d, J=6.3 Hz, 2H), 5.06 (br. s., 2H), 7.07 (dd, J=6.9, 1.9 Hz, 3H), 7.10-7.18 (m, 3H), 7.23 (d, J=5.1 Hz, 1H), 7.35-7.40 (m, 2H), 7.60-7.63 (m, 2H). MS (ES+): m/z 416.34 (100) [MH+]. HPLC: tR=2.34 min (polar—5 min).

Workup

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

Sources & evidence

ORD record
ord-df362799c32b44b1896f735f2a40ff1f
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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