5-Amino-1-phenylbenzimidazole → HCID 59373121, compound

HRID 1471338Notes

Reaction equation

HRID 1471338 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][O:13][CH2:14][C:15]#[CH:16])=[N:4][N:3]=1.[NH2:17][C:18]1[CH:32]=[CH:31][C:21]2[N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:23]=[N:24][C:20]=2[CH:19]=1>CC(O)C>[C:25]1([N:22]2[C:21]3[CH:31]=[CH:32][C:18]([NH:17][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]([CH2:12][O:13][CH2:14][C:15]#[CH:16])=[N:4][N:3]=4)=[CH:19][C:20]=3[N:24]=[CH:23]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 9653125-Amino-1-phenylbenzimidazoleHCID 59372952HCID 59372952, compound

Product 1

HCID 59373121HCID 59373121, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1-chloro-4-(prop-2-ynyloxy)methylphthalazine (3) (20 mg, 0.09 mmol) and 5-amino-1-phenylbenzimidazole (15 mg, 0.07 mmol) in i-PrOH (2 mL) is stirred at 95° C. under argon for 2.5 h. The reaction mixture is concentrated, quenched with sat. NaHCO3 (10 mL), and extracted with CHCl3 (60 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (0:1:2 to 1:25:0 methanol/ethyl acetate/hexane) to give 8 mg (27%) of BI-3035 as a light-brown solid, mp 89-91° C. IR 3321, 2927, 1496 cm−1; 1H NMR (CDCl3) δ 2.60 (t, J=2.4 Hz, 1H, CH≡C—CH2O), 4.98 (s, 2H, CH2), 5.36 (d, J=2.4 Hz, CH≡CCH2O), 6.94 (dd, J=8.7, 2.1 Hz, 1H, 6-BenzimidH), 7.27 (d, J=2.1 Hz, 1H, 4-BenzimidH), 7.41 (d, J=8.7 Hz, 1H, 7-BenzimidH), 7.41-7.63 (m, 5H, PhH), 7.90-8.02 (m, 2H, 6,7-PhthH), 8.06 (s, 1H, 2-BenzimidH), 8.14 (m, 1H, 5-PhthH), 8.35 (m, 1H, 8-PhthH).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customquenched with sat. NaHCO3 (10 mL)
  3. extractionextracted with CHCl3 (60 mL)
  4. washThe extract is washed (brine)
  5. customdried
  6. customAfter solvent removal at reduced pressure
  7. customthe residue is purified on silica gel (0:1:2 to 1:25:0 methanol/ethyl acetate/hexane)

Sources & evidence

ORD record
ord-75c31f9cac3947318e91b669617d3351
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

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