tert-butyl [7-[amino(hydroxyimino)methyl]-3,4-dihydroisoquinolin-2(1H)-yl]acetate → tert-butyl [7-{5-[4-(2-ethylpiperidin-1-yl)-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}-3,4-dihydroisoquinolin-2(1H)-yl]acetate

HRID 400784Notes

Reaction equation

HRID 400784 reaction equation
Cl.[CH2:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][C:11]=1[CH2:19][O:20][CH3:21])[CH3:3].[NH2:22][C:23](=[N:42]O)[C:24]1[CH:33]=[C:32]2[C:27]([CH2:28][CH2:29][N:30]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31]2)=[CH:26][CH:25]=1>CCOC(C)=O>[CH2:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:10]1[CH:18]=[CH:17][C:13]([C:14]2[O:16][N:22]=[C:23]([C:24]3[CH:33]=[C:32]4[C:27]([CH2:28][CH2:29][N:30]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31]4)=[CH:26][CH:25]=3)[N:42]=2)=[CH:12][C:11]=1[CH2:19][O:20][CH3:21])[CH3:3]

Participants

4

Reactant 2

HCID 76787421tert-butyl [7-[amino(hydroxyimino)methyl]-3,4-dihydroisoquinolin-2(1H)-yl]acetateHCID 1317314304-(2-Ethylpiperidin-1-yl)-3-(methoxymethyl)benzoic acid hydrochloride

Product 1

HCID 68653561tert-butyl [7-{5-[4-(2-ethylpiperidin-1-yl)-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}-3,4-dihydroisoquinolin-2(1H)-yl]acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Title compound was prepared following general procedure 2 starting from Intermediate 22 (188 mg; 0.6 mmol) and Intermediate 5 (174 mg; 0.6 mmol). The reaction mixture was diluted with EtOAc, washed with water and brine and evaporated under vacuum.

Workup

  1. washwashed with water and brine
  2. customevaporated under vacuum

Sources & evidence

ORD record
ord-89ddd36e512946a7812b9b8f2d18a2b8
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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