Ammonium Hydroxide → HCID 178480630, compound

HRID 479979Notes

Reaction equation

HRID 479979 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 B4NOH 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 505 (1.485 g, 3.87 mmol) in DMF (30 mL) was added to the teirabutyl 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 514 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-b463aa4324b84efb8c538f2427c2148e
Source dataset
uspto-grants-2003_11
Patent number
US06649587B1

Reaction notes

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