Hydrazine hydrate (1:1) → N1-(1H-Benzoimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydroquinoxalin-5-yl)-butane-1,4-diamine

HRID 899816Notes

Reaction equation

HRID 899816 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][N:18]([CH2:29][CH2:30][CH2:31][CH2:32][N:33]1C(=O)C2C(=CC=CC=2)C1=O)[CH:19]1[CH2:28][CH2:27][CH2:26][C:25]2[N:24]=[CH:23][CH:22]=[N:21][C:20]1=2)=O)(C)(C)C.O.NN>C(O)C>[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][N:18]([CH:19]1[CH2:28][CH2:27][CH2:26][C:25]2[N:24]=[CH:23][CH:22]=[N:21][C:20]1=2)[CH2:29][CH2:30][CH2:31][CH2:32][NH2:33]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 692063402-{[[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-(5,6,7,8-tetrahydroquinoxalin-5-yl)-amino]-methyl}-benzoimidazole-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 10193611N1-(1H-Benzoimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydroquinoxalin-5-yl)-butane-1,4-diamineYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-{[[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-(5,6,7,8-tetrahydroquinoxalin-5-yl)-amino]-methyl}-benzoimidazole-1-carboxylic acid tert-butyl ester (420 mg, 0.723 mmol) in ethanol (20 mL) at room temperature was added hydrazine hydrate (0.20 mL). The mixture was stirred for 17 hours. The mixture was concentrated in vaccuo and the resultant material was purified by column chromatography on silica gel (1:1:10 MeOH:NH4OH:CH2Cl2) to provide COMPOUND 105 as a colourless foam (161 mg, 64%): 1H NMR (CDCl3) δ 1.37-1.48 (m, 5H), 1.70-1.79 (m, 1H), 1.81-1.97 (m, 1H), 2.07-2.16 (m, 1H), 2.18-2.31 (m, 1H), 2.49-2.59 (m, 4H), 2.71-2.78 (m, 1H), 2.90-3.08 (m, 2H), 3.98 (d, 1H, J=16.5 Hz), 4.07 (d, 1H, J=16.5 Hz), 4.06-4.12 (m, 1H), 7.18-7.21 (m, 2H), 7.57-7.59 (m, 2H), 8.41 (s, 1H), 8.54 (s, 1H); 13C NMR (CDCl3) δ 21.2, 22.9, 26.3, 30.5, 32.6, 41.7, 49.8, 51.4, 62.0, 122.3, 142.1, 143.3, 153.8, 155.4, 155.5; ES-MS m/z 351 (M+H). Anal. Calcd. for C20H26N6.0.3CH2Cl2.0.2H2O: C, 64.24; H, 7.17; N, 22.14. Found: C, 64.16; H, 7.41; N, 22.15.

Workup

  1. concentrationThe mixture was concentrated in vaccuo
  2. customthe resultant material was purified by column chromatography on silica gel (1:1:10 MeOH:NH4OH:CH2Cl2)

Sources & evidence

ORD record
ord-4d6cd21b93ff41849a0d5c97a6e68e95
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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