1-Chloro-4-phenylphthalazine → HCID 1386209, compound

HRID 1471331Notes

Reaction equation

HRID 1471331 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:3]=1.[NH2:18][C:19]1[CH:33]=[CH:32][C:22]2[N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:24]=[N:25][C:21]=2[CH:20]=1>CC(O)C>[C:26]1([N:23]2[C:22]3[CH:32]=[CH:33][C:19]([NH:18][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)=[N:4][N:3]=4)=[CH:20][C:21]=3[N:25]=[CH:24]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 2721091-Chloro-4-phenylphthalazineHCID 9653125-Amino-1-phenylbenzimidazole

Product 1

HCID 1386209HCID 1386209, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1-chloro-4-phenylphthalazine (156 mg, 0.65 mmol) and 5-amino-1-phenylbenzimidazole (4) (105 mg, 0.5 mmol) in i-PrOH (10 mL) is stirred at 95° C. under argon for 2 h. The reaction mixture is concentrated, diluted with sat. NaHCO3 (15 mL), and extracted with CHCl3 (100 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (1% to 9% methanol/ethyl acetate) to give 206 mg (99%) of 5 as an orange solid, mp 265° C. IR 3285, 2842, 1615, 1476 cm−1; 1H NMR (CDCl3) δ 7.45-7.61 (m, 5H, 1-PhH), 7.62-7.77 (m, 6H, 4′-C6H5, 7-BenzimidH), 7.82 (dd, J=8.7, 2.1 Hz, 1H, 6-BenzimidH), 7.86-7.90 (m, 1H, 5′-PhthH), 7.91-7.98 (m, 1H, 6′-PhthH), 8.00-8.08 (m, 1H, 7′-PhthH), 8.50 (d, J=2.1 Hz, 1H, 4-BenzimidH), 8.56 (s, 1H, 2-BenzimidH), 8.72 (d, J=8.7 Hz, 1H, 8′-PhthH), 9.37 ppm (s, 1H, NH).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additiondiluted with sat. NaHCO3 (15 mL)
  3. extractionextracted with CHCl3 (100 mL)
  4. washThe extract is washed (brine)
  5. customdried
  6. customAfter solvent removal at reduced pressure
  7. customthe residue is purified on silica gel (1% to 9% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-4c937f03d04c4d04957890f17d701a28
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

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