1-Chloro-4-methylphthalazine → 5-Amino-1-phenylbenzimidazole

HRID 1471339노트

반응식

HRID 1471339 반응식
ClC1C2C(=CC=CC=2)C(C)=NN=1.[NH2:13][C:14]1[CH:34]=[CH:33][C:17]2[N:18]([C:21]3[CH:26]=[CH:25][C:24](C4C=CC=CC=4)=[CH:23][CH:22]=3)[CH:19]=[N:20][C:16]=2[CH:15]=1>CC(O)C>[NH2:13][C:14]1[CH:34]=[CH:33][C:17]2[N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=[N:20][C:16]=2[CH:15]=1

참가 물질

4

반응물 2

HCID 2697331-Chloro-4-methylphthalazineHCID 13024894HCID 13024894, 화합물

생성물 1

HCID 9653125-Amino-1-phenylbenzimidazole수율 181.6%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution of 1-chloro-4-methylphthalazine (25 mg, 0.14 mmol) and 5-amino-1-(biphen-4-yl)benzimidazole (3) (28.5 mg, 0.10 mmol) in i-PrOH (2 mL) is stirred at 95° C. under argon for 2.5 h, cooled to room temperature, and concentrated at reduced pressure. The residue is diluted with sat. NaHCO3 (15 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 (3.2% to 4.8% methanol/ethyl acetate) to give 38 mg (88%) of 4 (BI-3039) as a light-brown solid, mp 272-274° C. IR 3339, 2979, 1522, 1412 cm−1; 1H NMR (CD3OD/CDCl3) δ 2.82 (s, 3H, CH3), 7.36-7.53 (m, 3H, PhH), 7.62 (d, J=9.00 Hz, 1H, 7-BenzimidH), 7.69 (m, 2H, Aril, 2H PhH), 7.79 (d, J=8.7 Hz, 1H, 6-BenzimidH), 7.86 (d, J=8.1 Hz, 2H, ArH), 7.91-7.98 (m, 2H, 6,7-PhthH), 8.07 (m, 1H, 5-PhthH), 8.10 (s, 1H, 4-BenzimidH), 8.32 (s, 1H, 2-BenzimidH), 8.45 ppm (m, 1H, 8-PhthH).

후처리

  1. concentrationconcentrated at reduced pressure
  2. additionThe residue is diluted with sat. NaHCO3 (15 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 (3.2% to 4.8% methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-a243f4a8db75461eba0da2f8152b8a0e
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012217B2

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