Diisopropylethylamine → 6-[1-hydroxy-2-(4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-3-methyl-3,4-dihydro-1H-isochromen-1-one

HRID 2173455Notes

Reaction equation

HRID 2173455 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:12]3[CH2:14][O:13]3)[CH:9]=2)[C:4](=[O:15])[O:3]1.Cl.[N:17]1([C:23](=[O:36])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH:35]=[N:34][N:33]=[N:32]3)=[CH:27][CH:26]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.CCN(C(C)C)C(C)C>CCO>[OH:13][CH:12]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4](=[O:15])[O:3][CH:2]([CH3:1])[CH2:11]2)[CH2:14][N:20]1[CH2:19][CH2:18][N:17]([C:23](=[O:36])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([N:31]3[CH:35]=[N:34][N:33]=[N:32]3)=[CH:29][CH:30]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 675172361-(piperazin-1-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone hydrochlorideHCID 772306793-methyl-6-(oxiran-2-yl)-3,4-dihydro-1H-isochromen-1-one

Product 1

HCID 866930426-[1-hydroxy-2-(4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-3-methyl-3,4-dihydro-1H-isochromen-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A sealed tube containing 3-methyl-6-(oxiran-2-yl)-3,4-dihydro-1H-isochromen-1-one (72 mg, 35 mmol), 1-(piperazin-1-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone hydrochloride (109 mg, 0.35 mmol), DIEA (0.2 mL) and EtOH (3 mL) was heated to 80 C for 12 hours. The excess solvent was removed and the crude product purified via MPLC (35% EtOAc/Hex-60% EtOAc/Hex) to give 6-[1-hydroxy-2-(4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-3-methyl-3,4-dihydro-1H-isochromen-1-one. LC-MS (IE, m/z): 477 [M+1]+.

Workup

  1. temperaturewas heated to 80 C for 12 hours
  2. customThe excess solvent was removed
  3. customthe crude product purified via MPLC (35% EtOAc/Hex-60% EtOAc/Hex)

Sources & evidence

ORD record
ord-58d583cdb2374ad1820f5116b9ddc4a3
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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