Formic Acid → HCID 57949592, compound

HRID 2427772Notes

Reaction equation

HRID 2427772 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:24][N:25]([CH3:33])[CH2:26][CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.[CH:34](O)=O.C=O.C([BH3-])#N.[Na+]>CO.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:24][N:25]([CH3:33])[CH2:26][CH:27]2[CH2:28][CH2:29][N:30]([CH3:34])[CH2:31][CH2:32]2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]([F:23])([F:21])[F:22])=[CH:17][CH:18]=1)[CH2:7]2

Participants

7

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57949376HCID 57949376, compound

Product 1

HCID 57949592HCID 57949592, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7-Methyl-5-[(methyl-piperidin-4-ylmethyl-amino)-methyl]-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (30 mg, 0.065 mmol) in methanol (1.5 mL) was added formic acid (0.02 ml), formaldehyde (0.1 mL), and Sodium cyanoborohydride (0.2 mL, 0.1 M in THF) respectively. The mixture stirred at room temperature for 1 hour and was then diluted with water and extracted with ethyl acetate. The organics were washed with brin, dried over anhydrous sodium sulfate, filtered and concentrated to provide the title compound (15 mg, 38%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.35 (d, 2H), 7.21-7.14 (m, 4H), 4.78 (s, 2H), 4.22 (s, 2H), 3.48 (s, 2H), 2.94 (d, 2H), 2.75 (s, 3H), 2.33 (s, 3H), 2.23 (d, 2H), 2.16 (s, 3H), 2.01 (t, 2H), 1.84-1.80 (m, 2H), 1.54-1.51 (m, 1H), 1.25-1.20 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organics were washed
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aa08d6173eb9442ab6408816a1e3e619
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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