Hydrazine hydrate (1:1) → HCID 69294294, compound

HRID 899742Notes

Reaction equation

HRID 899742 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([CH2:21][N:22]([CH:38]3[C:47]4[N:46]=[CH:45][CH:44]=[CH:43][C:42]=4[CH2:41][CH2:40][CH2:39]3)[CH2:23][CH2:24][CH2:25][CH2:26][N:27]3C(=O)C4C(=CC=CC=4)C3=O)=[N:10][CH:9]=2)=[CH:4][CH:3]=1.O.NN>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:19])([CH3:20])[CH3:18])[C:11]([CH2:21][N:22]([CH:38]3[C:47]4[N:46]=[CH:45][CH:44]=[CH:43][C:42]=4[CH2:41][CH2:40][CH2:39]3)[CH2:23][CH2:24][CH2:25][CH2:26][NH2:27])=[N:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69178429HCID 69178429, compound

Product 1

HCID 69294294HCID 69294294, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-{4-[[5-(4-Fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8yl)-amino]-butyl}-isoindole-1,3-dione (0.3125 g, 0.48 mmol) in ethanol (5 mL) was added hydrazine monohydrate (0.12 mL), and the reaction mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated, and purified via column chromatography on silica gel (20:1:1 CH2Cl2-MeOH—NH4OH) to yield 0.1838 g (73%) of N1-[5-(4-Fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-ylmethyl]-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine. 1H NMR (CDCl3) δ 0.85 (t, 2H, J=8.1 Hz), 1.25-1.34 (m, 7H), 1.61-1.72 (m, 1H), 1.89-2.05 (m, 4H), 2.54-2.82 (m, 8H), 3.35-3.47 (m, 3H), 3.93 (s, 2H), 4.06 (t, 1H, J=8.1 Hz), 5.53 (d, 2H, J=10.5 Hz), 5.78 (d, 2H, J=10.8 Hz), 6.99-7.04 (m, 3H), 7.15 (s, 1H), 7.31 (d, 1H, J=7.5 Hz), 7.66-7.70 (m, 2H), 8.47 (d, 1H, J=3.6 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified via column chromatography on silica gel (20:1:1 CH2Cl2-MeOH—NH4OH)

Sources & evidence

ORD record
ord-3f82b239c40c4abdbe7f8e50f0a0ebce
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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