Dichloromethane → 2-Cycloheptyl-N-[2-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-acetamide

HRID 1037767Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH2:13][C:14]1[CH:23]=[CH:22][C:17]3[O:18][CH2:19][CH2:20][O:21][C:16]=3[CH:15]=1)[C:7]2=[O:12].[CH:24]1([CH2:31][C:32](O)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.F[P-](F)(F)(F)(F)F.FC(N(C)C)=[N+](C)C.C(N(CC)C(C)C)(C)C.C(Cl)Cl>>[CH:24]1([CH2:31][C:32]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]([CH2:13][C:14]2[CH:23]=[CH:22][C:17]4[O:18][CH2:19][CH2:20][O:21][C:16]=4[CH:15]=2)[C:7]3=[O:12])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

Reactant 5

HCID 6344Dichloromethane

HCID 81531Diisopropylethylamine

HCID 2274012-Cycloheptylacetic acid

HCID 2774761Tetramethylfluoroformamidinium hexafluorophosphate

HCID 582704495-Amino-2-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-2H-isoquinolin-1-one

Product 1

HCID 167425592-Cycloheptyl-N-[2-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-acetamide

Procedure

5-Amino-2-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-2H-isoquinolin-1-one (50 mg, 0.0002 mol), 2-cycloheptylacetic acid (63 mg, 0.00041 mol), fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (110 mg, 0.00041 mol) and N,N-diisopropylethylamine (100 mg, 0.0008 mol) were stirred in methylene chloride (3 mL, 0.05 mol) at room temperature for 72 hours. The mixture was purified via flash chromatography (12 g of silica gel, 50% EtOAc/Hexane) to give a light yellow solid.

Workup

customThe mixture was purified via flash chromatography (12 g of silica gel, 50% EtOAc/Hexane)
customto give a light yellow solid

Sources & evidence

ORD record: ord-7b26a8bc765c44e693fb51813cdea3b4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546579B2

Reaction notes

Loading…