Hydrazine hydrate (1:1) → HCID 59694133, compound

HRID 1624325Notes

Reaction equation

HRID 1624325 reaction equation
[F:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][N:12]([CH:28]3[C:37]4[N:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH2:31][CH2:30][CH2:29]3)[CH2:13][CH2:14][CH2:15][CH2:16][N:17]3C(=O)C4C(=CC=CC=4)C3=O)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C.C(OCC)C>[F:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][N:12]([CH:28]3[C:37]4[N:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH2:31][CH2:30][CH2:29]3)[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69294583HCID 69294583, compound

Product 1

HCID 59694133HCID 59694133, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2-{4-[(4-fluoro-1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione (86 mg, 0.173 mmol) in ethanol (2.0 mL) was added hydrazine hydrate (0.05 mL, 1.03 mmol) and the mixture stirred at room temperature for 20 hours. The mixture was then diluted with diethyl ether, dried (MgSO4), filtered and concentrated under reduced pressure to give a crude yellow oil. The oil was purified by flash chromatography (1.75 cm ID, 12 g silica, 25:1:1 CH2Cl2: MeOH: NH4OH) to give pure N1-(4-fluoro-1H-benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (29 mg, 46%). 1H NMR (CDCl3) δ 1.28-1.47 (m, 4H), 1.63-1.77 (m, 1H), 1.85-2.09 (m, 2H), 2.15-2.25 (m, 1H), 2.46-2.60 (m, 3H), 2.65-2.76 (m, 2H), 2.79-2.91 (m, 1H), 4.01-4.18 (m, 3H), 6.89 (dd, 1H, J=10.3, 8.0 Hz), 7.05-7.11 (m, 1H), 7.12-7.18 (m, 1H), 7.35 (d, 1H, J=7.8 Hz), 7.43 (d, 1H, J=7.9 Hz), 8.59 (d, 1H, J=4.4 Hz).

Workup

  1. dry with materialdried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude yellow oil
  5. customThe oil was purified by flash chromatography (1.75 cm ID, 12 g silica, 25:1:1 CH2Cl2: MeOH: NH4OH)

Sources & evidence

ORD record
ord-7f888fc5ecdc46778a02d6e6ee45fc87
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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