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

HRID 899597Notes

Reaction equation

HRID 899597 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-8-yl)-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 N-[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-13a37a6cdeb04492b12af4e7131e5274
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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