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

HRID 899679Notes

Reaction equation

HRID 899679 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-bdfb718129f04dc5a8a5da695f5facca
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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