Hydrazine → HCID 11338529, compound

HRID 2373907Notes

Reaction equation

HRID 2373907 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:37]3[CH2:40][CH2:39][CH2:38]3)=[N:9][C:10]=2[C:11]2[CH:12]=[C:13]([CH:34]=[CH:35][CH:36]=2)[O:14][CH2:15][C:16]2[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=2)[CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[CH:6][N:7]=1.NN>CCO>[NH2:20][CH2:19][C:18]1[CH:17]=[C:16]([CH:33]=[CH:32][CH:31]=1)[CH2:15][O:14][C:13]1[CH:12]=[C:11]([C:10]2[N:9]=[C:8]([CH:37]3[CH2:40][CH2:39][CH2:38]3)[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=23)[CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 11330005HCID 11330005, compound

Product 1

HCID 11338529HCID 11338529, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-{3-[3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenoxymethyl]-benzyl}-isoindole-1,3-dione (100 mg, 0.19 mmol) was dissolved in EtOH (0.76 mL) and charged with hydrazine (60 mg, 1.89 mmol) and stirred overnight at rt. The white ppt filtered and washed with EtOH. The filtrate was concentrated in vacuo, silica gel was added in CH2Cl2, and concentrated to solid. The product was chromatographed on silica gel [Jones Flashmaster, 2 g cartridge, eluting with ˜2% 7N NH3 MeOH:CH2Cl2] and isolated the title compound as a yellow solid; 1H NMR (CDCl3, 400 MHz) δ 1.84-1.92 (m, 1H), 1.97-2.09 (m, 1H), 2.34-2.40 (m, 2H), 2.44-2.46 (m, 2H), 3.69 (s, 2H), 3.84-3.92 (m, 1H), 5.10 (s, 2H), 6.96 (d, J=5.2 Hz, 1H), 7.01-7.03 (m, 1H), 7.13-7.16 (m, 1H), 7.18-7.19 (m, 1H), 7.23-7.32 (m, 3H), 7.35-7.40 (m, 3H); MS (ES+): m/z 400.17 (100) [MH+].

Workup

  1. filtrationThe white ppt filtered
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated in vacuo, silica gel
  4. additionwas added in CH2Cl2
  5. concentrationconcentrated to solid
  6. customThe product was chromatographed on silica gel [Jones Flashmaster, 2 g cartridge, eluting with ˜2% 7N NH3 MeOH:CH2Cl2]

Sources & evidence

ORD record
ord-9377cc750c0446e380c09ff32d97169f
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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