Dichloromethane → 2-Cycloheptyl-N-[1-oxo-2-(tetrahydro-pyran-4-ylmethyl)-1,2-dihydro-iso quinolin-5-yl]-acetamide

HRID 1037773Notes

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][CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:7]2=[O:12].[CH:20]1([CH2:27][C:28](O)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]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:20]1([CH2:27][C:28]([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][CH:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[C:7]3=[O:12])=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

Reactant 5

HCID 6344Dichloromethane

HCID 81531Diisopropylethylamine

HCID 2274012-Cycloheptylacetic acid

HCID 2774761Tetramethylfluoroformamidinium hexafluorophosphate

HCID 595796435-Amino-2-(tetrahydro-pyran-4-ylmethyl)-2H-isoquinolin-1-one

Product 1

HCID 595794432-Cycloheptyl-N-[1-oxo-2-(tetrahydro-pyran-4-ylmethyl)-1,2-dihydro-iso quinolin-5-yl]-acetamide

Procedure

5-Amino-2-(tetrahydro-pyran-4-ylmethyl)-2H-isoquinolin-1-one (40 mg, 0.0002 mot), 2-cycloheptylacetic acid (63 mg, 0.00041 mol), fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (110 mg, 0.00041 mol), N,N-diisopropylethylamine (100 mg, 0.0008 mol) were stirred in methylene chloride (3 mL, 0.05 mol) at room temperature over 72 hours. The mixture was purified via flash chromatography (12 g of silica gel, 0-50% EtOAc/Hexane) to give a light yellow solid.

Workup

customThe mixture was purified via flash chromatography (12 g of silica gel, 0-50% EtOAc/Hexane)
customto give a light yellow solid

Sources & evidence

ORD record: ord-e8d2953e2c85404db5557f62a6e1ce37
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546579B2

Reaction notes

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