Dichloromethane → (3-Chloropyrazin-2-yl)(2-phenylquinolin-7-yl)methanamine

HRID 1992417Notes

Reaction equation

HRID 1992417 reaction equation
[Cl:1][C:2]1[C:3]([CH:8]([C:20]2[CH:29]=[C:28]3[C:23]([CH:24]=[CH:25][C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[N:27]3)=[CH:22][CH:21]=2)[N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[N:4][CH:5]=[CH:6][N:7]=1.NN.C(Cl)Cl>CCO>[Cl:1][C:2]1[C:3]([CH:8]([NH2:9])[C:20]2[CH:29]=[C:28]3[C:23]([CH:24]=[CH:25][C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[N:27]3)=[CH:22][CH:21]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 536290132-((3-Chloropyrazin-2-yl)(2-phenylquinolin-7-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 51051365(3-Chloropyrazin-2-yl)(2-phenylquinolin-7-yl)methanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[(3-chloropyrazin-2-yl)-(2-phenylquinolin-7-yl)-methyl]-isoindole-1,3-dione (1.536 g, 3.22 mmol) and anhydrous hydrazine (335 μL, 342 mg, 10.7 mmol) in EtOH (2 mL)/CH2Cl2 (12 mL) is stirred at rt overnight. The white precipitate formed is filtered off and washed with CH2Cl2. The combined filtrate and washings are concentrated in vacuo, the residue is suspended in CDCl3 and filtered (0.45 μM pore size), and the filtrate is concentrated in vacuo to obtain the title compound as yellow foam, which is used for the next step without further purification; 1H NMR (CDCl3, 400 MHz): δ2.4 (brs, 2H), 5.79 (s, 1H), 7.43-7.55 (m, 3H), 7.61 (dd, J=1.8, 8.6 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.86 (d, J=8.4 Hz, 1H), 8.06 (d, J=1.2 Hz, 1H), 8.10-8.15 (m, 2H), 8.19 (d, J=8.8 Hz, 1H), 8.31 (d, J=2.4 Hz, 1H), 8.60 (d, J=2.4 Hz, 1H); MS (ES+):m/z347.0/349.0(30/10) [MH+], 330.0/332.0 (18/6) [MH+-NH3]; HPLC: tR=2.1 min (MicromassZQ, polar—5 min).

Workup

  1. customThe white precipitate formed
  2. filtrationis filtered off
  3. washwashed with CH2Cl2
  4. concentrationThe combined filtrate and washings are concentrated in vacuo
  5. filtrationfiltered (0.45 μM pore size)
  6. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-72842026780a45dd9dc6297441bf4951
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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