Hydrazine hydrate (1:1) → HCID 59694171, compound

HRID 899789Notes

Reaction equation

HRID 899789 reaction equation
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH:27]1[C:36]2[N:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH2:30][CH2:29][CH2:28]1)[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH:27]1[C:36]2[N:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH2:30][CH2:29][CH2:28]1)[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69156281HCID 69156281, compound

Product 1

HCID 59694171HCID 59694171, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-{4-[(4,5,6,7-tetrahydro-1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione (0.2466 g, 0.51 mmol) in ethanol (5 mL) was added hydrazine hydrate (0.3 mL, 2.5 mmol), and stirred at room temperature for 18 hours. The reaction mixture was concentrated, and purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2—MeOH—NH4OH) provided 0.1031 g (58%) of COMPOUND 89 as a pale yellow solid. 1H NMR (CDCl3) δ 1.32-1.43 (m, 5H), 1.60-1.68 (m, 1H), 1.72-1.81 (m, 5H), 1.96-2.02 (m, 1H), 2.08-2.17 (m, 1H), 2.45-2.60 (m, 9H), 2.69-2.71 (m, 1H), 2.76-2.86 (m, 1H), 3.70-3.84 (m, 2H), 3.95-4.01 (m, 1H), 7.05-7.10 (m, 1H), 7.36 (d, 1H, J=7.5 Hz), 8.44 (d, 1H, J=3 Hz). 13C NMR (CDCL3) δ 20.80, 22.38, 22.71, 23.07, 25.37, 28.77, 30.54, 41.23, 48.53, 49.81, 60.54, 121.36, 133.94, 136.52, 146.20, 146.32, 157.37. ES-MS m/z 354.5 (M+H). Anal. Calcd. for (C21H31N5)0.7(H2O)0.1(CH2Cl2): C, 67.65; H, 8.77; N, 18.69. Found: C, 67.46; H, 8.80; N, 18.43.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2—MeOH—NH4OH)

Sources & evidence

ORD record
ord-35ff2fe6c9504f248c77631659251627
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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