Hydrazine → HCID 178511227, compound

HRID 386168Notes

Reaction equation

HRID 386168 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:27]3[CH2:32][CH2:31][C@H:30]([CH2:33][N:34]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:29][CH2:28]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.NN>>[NH2:34][CH2:33][C@H:30]1[CH2:31][CH2:32][C@H:27]([C:8]2[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]3=[C:10]([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[N:18]4)=[CH:13][CH:12]=3)[N:9]=2)[CH2:28][CH2:29]1

Participants

3

Reactant 2

HCID 9321HydrazineHCID 178508461HCID 178508461, compound

Product 1

HCID 178511227HCID 178511227, compound

Procedure

An ethanolic solution of trans-2-{4-[8-Amino-1-(2-phenylquinolin-7-yl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexylmethyl}-isoindole-1,3-dione (265 mg, 0.46 mmol) was charged with an excess of hydrazine (0.14 mL, 4.6 mmol) and allowed to stir at rt for 16 h. The solution was filtered through a fritted glass funnel and the solids were washed with EtOH (4×). The filtrate was concentrated and the crude material was purified by silica gel column chromatography [Jones Flashmaster, 5 g/25 mL cartridge, eluting with 2%˜7 N NH3 in MeOH/CH2Cl2 to 4%˜7N NH3 in MeOH/CH2Cl2]. The purified material was recrystallized from CH2Cl2/hexanes to afford the desired product as a yellow solid; 1H NMR (CDCl3, 400 MHz) δ 1.16-1.26 (m, 2H), 1.58-1.65 (m, 1H), 1.87-1.99 (m, 2H), 2.02-2.09 (m, 2H), 2.13-2.22 (m, 2H), 2.72 (d, 2H, J=6.4 Hz), 2.92-3.01 (m, 1H), 7.10 (d, 1H, J=5.2 Hz), 7.25-7.28 (m, 1H), 7.42-7.55 (m, 3H), 7.89-7.94 (m, 3H), 8.18-8.20 (m, 2H), 8.24 (d, 1H, J=8.8 Hz), 8.39-8.41 (m, 1H); MS (ES+): m/z 449.0 [MH+]; HPLC: tR=2.0 min (Micromass Platform II, nonpolar—5 min).

Workup

  1. filtrationThe solution was filtered through a fritted glass funnel
  2. washthe solids were washed with EtOH (4×)
  3. concentrationThe filtrate was concentrated
  4. customthe crude material was purified by silica gel column chromatography [Jones Flashmaster, 5 g/25 mL cartridge, eluting with 2%˜7 N NH3 in MeOH/CH2Cl2 to 4%˜7N NH3 in MeOH/CH2Cl2]
  5. customThe purified material was recrystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-bc7030628af0492bbb11788158cb1aa1
Source dataset
uspto-grants-2013_02
Patent number
US08367826B2

Reaction notes

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