Acetaldehyde → HCID 59699297, compound

HRID 2237070Notes

Reaction equation

HRID 2237070 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]2[N:9]([C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]4[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=4)=[CH:30][CH:29]=3)[CH:10]=[C:11]([C:13]3[CH:27]=[CH:26][C:16]([O:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:15][CH:14]=3)[N:12]=2)[CH2:3][CH2:2]1.[CH:42](=O)[CH3:43].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:42]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]2[N:9]([C:28]3[CH:29]=[CH:30][C:31]([O:34][C:35]4[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=4)=[CH:32][CH:33]=3)[CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:26][CH:27]=3)[N:12]=2)[CH2:3][CH2:2]1)[CH3:43]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59699227[3-(4-{2-(Piperidine-4-ylmethyl)-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethyl-amine

Product 1

HCID 59699297HCID 59699297, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-(4-{2-(Piperidine-4-ylmethyl)-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethyl-amine (Example 539) (0.1 mmol) was treated in anhydrous DCM (2 ml) with acetaldehyde (1.2 eq.) followed by addition of Na(OAc)3BH (1.5 eq.). The reaction mixture was stirred at rt. Crude product was extracted into EtOAc and washed with saturated sodium bicarbonate solution. The organic layer was dried over anhydrous sodium sulfate and concenterated in vacuo to give desired product, which was purified by column chromatography on silica gel to afford 49 mg of Example 540.

Workup

  1. extractionCrude product was extracted into EtOAc
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-2e54003e203742f49d026f7da61b98b3
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Reaction notes

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