Sodium Bicarbonate → E-2110 free base

HRID 494940Notes

Reaction equation

HRID 494940 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)=[O:4].[CH3:20][O:21][C:22]1[C:31]([CH2:32][CH:33]=O)=[C:30]2[C:25]([C:26](=[O:37])[CH2:27][C:28]([CH3:36])([CH3:35])[O:29]2)=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:20][O:21][C:22]1[C:31]([CH2:32][CH2:33][N:17]2[CH2:18][CH2:19][CH:14]([N:11]3[C:12]4[C:8](=[CH:7][CH:6]=[C:5]([C:3]([NH:2][CH3:1])=[O:4])[CH:13]=4)[CH:9]=[CH:10]3)[CH2:15][CH2:16]2)=[C:30]2[C:25]([C:26](=[O:37])[CH2:27][C:28]([CH3:36])([CH3:35])[O:29]2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57682772(7-Methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehydeHCID 576828371-(piperidin-4-yl)-N-methyl-1H-indole-6-carboxamide

Product 1

HCID 11677552E-2110 free baseYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

120 mg of N-methyl-1-(piperidin-4-yl)-1H-indole-6-carboxamide and 120 mg of (7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehyde were dissolved in 8 ml of methylene chloride. Thereafter, 0.05 ml of acetic acid and 0.15 g of sodium triacetoxyborohydride were added to the reaction solution, and the obtained mixture was then stirred at room temperature for 1 hour. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by extraction with methylene chloride. The extract was dried over magnesium sulfate and then filtered. The filtrate was then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (methanol-ethyl acetate), so as to obtain 210 mg of the subject compound.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. dry with materialThe extract was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was then concentrated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methanol-ethyl acetate)

Sources & evidence

ORD record
ord-92a03df966f442c8be7f39df62293741
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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