Dichloromethane → C-(3-benzyloxyphenyl)-C-(3-chloropyrazin-2-yl)methylamine hydrochloride

HRID 1992412Notes

Reaction equation

HRID 1992412 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([C:27]2[C:32]([Cl:33])=[N:31][CH:30]=[CH:29][N:28]=2)[N:16]2C(=O)C3C(=CC=CC=3)C2=O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl>CCO>[ClH:33].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([NH2:16])[C:27]2[C:32]([Cl:33])=[N:31][CH:30]=[CH:29][N:28]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 598528332-[(3-Benzyloxy-phenyl)-(3-chloro-pyrazin-2-yl)-methyl]-isoindole-1,3-dione

Product 1

HCID 86604615C-(3-benzyloxyphenyl)-C-(3-chloropyrazin-2-yl)methylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[(3-benzyloxy-phenyl)-(3-chloro-pyrazin-2-yl)-methyl]-isoindole-1,3-dione (2.76 g, 6.05 mmol) was dissolved in EtOH (12 mL) and CH2Cl2 (4 mL) charged with N2H4 (0.57 mL, 18.16 mmol) and allowed to react for 16 h at rt. The white precipitate was filtered and washed with EtOAc. The filtrate and organic washings were concentrated in vacuo, and purified via HPFC using a 100 g Jones silica gel column (50% EtOAc: Hex to 5% MeOH: CH2Cl2) to yield the desired product as a reddish oil; 1H NMR (CDCl3, 400 MHz) δ 5.04 (s, 2H), 5.52 (s, 1H), 6.85-6.98 (m, 2H), 7.21-7.26 (m, 2H), 7.30-7.41 (m, 5H), 8.26 (d, 1H, J=2.5 Hz), 8.52 (d, 1H, J=2.5 Hz); MS (ES) 326.25 (M+1), 328.23 (M+3), 329.24 (M+4).

Workup

  1. customto react for 16 h at rt
  2. filtrationThe white precipitate was filtered
  3. washwashed with EtOAc
  4. concentrationThe filtrate and organic washings were concentrated in vacuo
  5. custompurified via HPFC

Sources & evidence

ORD record
ord-f593f02c8ba94827a54c7fa499d637e5
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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