Acetic Acid → HCID 60026569, compound

HRID 400682Notes

Reaction equation

HRID 400682 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]([OH:26])([CH2:16][C:17]1[NH:25][C:20]2=[CH:21][N:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1)[CH2:4][C:5]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)([CH3:7])[CH3:6].ClC(Cl)C.C(O)(=O)C.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>C(OCC)(=O)C.[OH-].[NH4+]>[F:28][C:2]([F:1])([F:27])[C:3]([CH2:16][C:17]1[NH:25][C:20]2=[CH:21][N:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1)([OH:26])[CH2:4][C:5]([CH3:7])([C:8]1[CH:15]=[CH:14][CH:13]=[C:10]([CH2:11][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH:9]=1)[CH3:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 8083MorpholineHCID 60026335HCID 60026335, compound

Product 1

HCID 60026569HCID 60026569, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of 3-[4,4,4-trifluoro-3-hydroxy-1,1-dimethyl-3-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)butyl]benzaldehyde (50 mg, 0.13 mmol), 3 mL of dichloroethane, and acetic acid (0.1 mL, 1.6 mmol) in an ice bath was added morpholine (0.28 mL, 3.20 mmol) in one batch. The solution was warmed to room temperature and stirred for 0.5 hours. Triacetoxy sodium borohyride (68 g, 0.32 mmol) was added in a single portion and the reaction stirred at room temperature for 3.0 hours. The solution was diluted with ethyl acetate and 3 mL of 3% ammonium hydroxide solution was added. The biphasic system was transferred to a separatory funnel and the aqueous layer was removed and back-extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and the solvent was evaporated in vacuo. The product was eluted from a flash chromatography column with dichloromethane-methanol, and evaporation of the solvent in vacuo yielded the title compound (27 mg, 45% yield).

Workup

  1. stirringthe reaction stirred at room temperature for 3.0 hours
  2. additionwas added
  3. customThe biphasic system was transferred to a separatory funnel
  4. customthe aqueous layer was removed
  5. extractionback-extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated in vacuo
  10. washThe product was eluted from a flash chromatography column with dichloromethane-methanol, and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-da229f08c89446c0938ddd3d4df8e65f
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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