Acetaldehyde → (4-{3-[Ethyl-(5-phenyl-pyridin-2-yl)-amino]-propylsulfanyl}-5-methoxy-2-methyl-phenoxy)-acetic acid methyl ester

HRID 1296051Notes

Reaction equation

HRID 1296051 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([S:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][N:20]=2)=[CH:8][C:7]=1[CH3:31].[CH:33](=O)[CH3:34].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClC(Cl)C.Cl.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([S:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:33][CH3:34])[C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:21][N:20]=2)=[CH:8][C:7]=1[CH3:31]

Participants

8

Reactant 6

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 20770841HCID 20770841, compound

Product 1

HCID 20770817(4-{3-[Ethyl-(5-phenyl-pyridin-2-yl)-amino]-propylsulfanyl}-5-methoxy-2-methyl-phenoxy)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Compound 64B (300 mg, 0.66 mmol), acetaldehyde (32 mg, 0.73 mmol), sodium triacetoxyborohydride (211 mg, 0.994 mmol), and 57 □l acetic acid were added to 5 ml dichloroethane and stirred at room temperature for 3 days. 1 eq more of aldehyde, sodium triacetoxyborohydride, and acetic acid were added and stirred 3 h more. 10 ml 2N HCl was added followed by saturated sodium bicarbonate to pH ca. 8. The product was extracted into 20 ml, dried over sodium sulfate, decanted, concentrated. Liquid chromatography give the title compound as a white solid. MS m/z 481 (M+1).

Workup

  1. stirringstirred 3 h more
  2. extractionThe product was extracted into 20 ml
  3. dry with materialdried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6bb67c47787449c3acc21a7eb41350d5
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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