Ammonium Hydroxide → HCID 178480630, compound

HRID 393875Notes

Reaction equation

HRID 393875 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[NH:16][C:15]([C:17]4[CH:18]=[CH:19][C:20]5[NH:25][C:24]([C:26]6[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=6)=[N:23][C:21]=5[CH:22]=4)=[N:14][C:12]=3[CH:13]=2)[CH2:4][CH2:3]1.[OH-].[NH4+]>C(O)(C)C.O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:16]=[C:15]([C:17]4[CH:18]=[CH:19][C:20]5[NH:25][C:24]([NH:23][C:21]=5[CH:22]=4)=[C:26]4[CH:27]=[CH:28][C:29](=[O:32])[CH:30]=[CH:31]4)[NH:14][C:12]=3[CH:13]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 178418289HCID 178418289, compound

Product 1

HCID 178480630HCID 178480630, compound

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

Hoechst 33258 (3.0 g, 5 mmol) was dissolved in a hot mixture of isopropanol-water (24 mL/12 mL) and neutralized with ammonium hydroxide (3 mL). The precipitate was filtered, triturated with Et2O and dried in vacuo to obtain the free base of bisbenzimidazole. A 1.0 M solution of Bu4NOH in MeOH (0.6 mL, 0.6 mmol) was added to the solution of bisbenzimidazole (1.635 g, 3.85 mmol) in MeOH (30 mL), stirred for 15 min and concentrated to dryness in vacuo. Iodonaphthoquinone 5 (1.485 g, 3.87 mmol) in DMF (30 mL) was added to the tetrabutyl ammonium salt and the mixture was stirred for 48 h. The reaction mixture was suspended in H2O, the crude product was filtered, washed with H2O, dried and purified by flash chromatography (MeOH/CHCl3 1:9, 1:5) to afford 14 as a yellow solid (790 mg, 30%). 1H NMR (CDCl3/MeOH-d4) 8.21 (s, 1H), 8.09 (d, J=7.6 Hz, 1H), 8.05 (d, J=8.7 Hz, 2H), 7.85-7.95 (m, 2H), 7.48-7.75 (m, 4H), 7.14 (bs, 1H), 7.10-6.98 (m 3H), 4.21 (t, J=6.3 Hz, 2H), 4.08 (t, J=6.2 Hz, 2H), 2.65-2.75 (m, 4H), 2.40 (s, 3H), 1.80-2.15 (m, 4H), 1.60-1.75 (m, 4H). MS (LSIMS, 3-NBA) 725.2 (M++1).

Workup

  1. filtrationThe precipitate was filtered
  2. customtriturated with Et2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-3b7bfa0ed4fb49d6a6cabe228d56cb27
Source dataset
uspto-grants-2004_10
Patent number
US06809176B2

Reaction notes

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