Acetic Acid → HCID 56970630, compound

HRID 1519626Notes

Reaction equation

HRID 1519626 reaction equation
Cl.[CH3:2][C:3]1[C:11]2[CH2:10][O:9][C:8](=[O:12])[C:7]=2[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[O:21]=[C:22]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][CH:32]=O)=[CH:30][C:25]=2[CH2:24][O:23]1.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[N:15]1([CH2:14][CH2:13][C:4]2[CH:5]=[CH:6][C:7]3[C:8](=[O:12])[O:9][CH2:10][C:11]=3[C:3]=2[CH3:2])[CH2:20][CH2:19][N:18]([CH2:32][CH2:31][C:29]2[CH:28]=[CH:27][C:26]3[C:22](=[O:21])[O:23][CH2:24][C:25]=3[C:30]=2[CH3:34])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 675172294-methyl-5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one hydrochlorideHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

Product 1

HCID 56970630HCID 56970630, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-methyl-5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one hydrochloride (62 mg, 0.21 mmol), (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (40 mg, 0.21 mmol), and sodium triacetoxyborohydride (67 mg, 0.32 mmol) in DCM (5 mL) was stirred overnight with a drop of acetic acid. LC showed formation of the desired product, which was purified by mass-directed HPLC (0.1% TFA in water and acetonitrile). LC-MS (IE, m/z): 435 [M+1]+. (0.076 μM)

Sources & evidence

ORD record
ord-7697c1be201c41a1bda9a39a5f6d95d4
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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