Acetic Acid → 3,5-Dimethoxy-4-methyl-N-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-phenethylamino-benzyl]-benzamide

HRID 1296744Notes

Reaction equation

HRID 1296744 reaction equation
C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:19][C:20]1[CH:40]=[C:39]([C:41]2[N:45]=[C:44]([CH3:46])[O:43][N:42]=2)[CH:38]=[CH:37][C:21]=1[CH2:22][NH:23][C:24](=[O:36])[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([CH3:33])=[C:27]([O:34][CH3:35])[CH:26]=1.[C:47]1([CH2:53][CH:54]=O)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>ClCCCl>[CH3:35][O:34][C:27]1[CH:26]=[C:25]([CH:30]=[C:29]([O:31][CH3:32])[C:28]=1[CH3:33])[C:24]([NH:23][CH2:22][C:21]1[CH:37]=[CH:38][C:39]([C:41]2[N:45]=[C:44]([CH3:46])[O:43][N:42]=2)=[CH:40][C:20]=1[NH:19][CH2:54][CH2:53][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:36]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 998PhenylacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69491883N-[2-Amino-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-3,5-dimethoxy-4-methyl-benzamide

Product 1

HCID 694916163,5-Dimethoxy-4-methyl-N-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-phenethylamino-benzyl]-benzamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Acetic acid (0.040 mL, 5 eq) and sodium triacetoxyborohydride (42 mg, 0.20 mmol) were added to a suspension of compound 1g (50 mg, 0.13 mmol) and phenylacetaldehyde (0.020 mg, 2 eq) in DCE (1.5 mL). The reaction was stirred at rt for 16 h and concentrated on a rotary evaporator. The residue was purified by preparative tlc (silica gel, 1:1 ethyl acetate/hexane) to afford compound 9a. ESI-MS m/e 487.3 (M+1).

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. customThe residue was purified by preparative tlc (silica gel, 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-afaf87626af9411ca3c157cdf49a6606
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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