Dichloromethane → 2-Cycloheptyl-N-(2-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

HRID 1037770Notes

Reaction equation

HRID 1037770 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]([CH3:13])[C:7]2=[O:12].[CH:14]1([CH2:21][C:22](O)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]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:14]1([CH2:21][C:22]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]([CH3:13])[C:7]3=[O:12])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 2274012-Cycloheptylacetic acidHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 122203445-Amino-2-methyl-1(2H)-isoquinolinone

Product 1

HCID 247855862-Cycloheptyl-N-(2-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

Procedure

5-Amino-2-methyl-2H-isoquinolin-1-one (50 mg, 0.0003 mol), 2-cycloheptylacetic acid (90 mg, 0.0006 mol), fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (200 mg, 0.0006 mol), N,N-diisopropylethylamine (100 mg, 0.0009 mol) were stirred in methylene chloride (2 mL, 0.03 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 yellow solid. 1H NMR δ (CDCl3) δ: 8.31 (d, J=7.9 Hz, 1H), 7.95-7.92 (m, 1H), 7.47 (t, J=7.9 Hz, 1H), 7.20 (br, 1H), 7.11 (d, J=7.6 Hz, 1H), 6.41 (d, J=7.5 Hz, 1H), 3.60 (s, 3H), 2.37 (d, J=7.3 Hz, 2H), 2.17 (br, 1H), 1.86-1.25 (12H).

Workup

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

Sources & evidence

ORD record
ord-545909074151480dbe79e6dc2f1b1cd5
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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