Isopropanol → HCID 1386209, 화합물

HRID 1471332노트

반응식

HRID 1471332 반응식
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.[CH2:18]([N:21]1[C:25]2[CH:26]=[CH:27][C:28]([NH2:30])=[CH:29][C:24]=2[N:23]=[CH:22]1)[C:19]#[CH:20].[CH3:31][CH:32](O)[CH3:33]>>[C:18]1([N:21]2[C:25]3[CH:26]=[CH:27][C:28]([NH:30][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:29][C:24]=3[N:23]=[CH:22]2)[CH:33]=[CH:32][CH:31]=[CH:20][CH:19]=1

참가 물질

4

반응물 3

HCID 3776IsopropanolHCID 2721091-Chloro-4-phenylphthalazineHCID 59372953HCID 59372953, 화합물

생성물 1

HCID 1386209HCID 1386209, 화합물수율 99%

실험 절차

A solution of 1-chloro-4-phenylphthalazine (81 mg, 0.34 mmol) and 1-(prop-2-ynyl)-5-aminobenzimidazole (3) (36 mg, 0.21 mmol) in i-PrOH (6 mL) is stirred at 95° C. under argon for 2 h and then concentrated. 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 (1% to 10% methanol/ethyl acetate) to give 78 mg (99%) of 5 (BI-3007) as a yellow solid, mp 227-229° C. IR 3304, 2965, 1495, 1401 cm−1; NMR (DMSO-d6) δ 3.54 (t, J=2.4 Hz, 1H, CH≡CCH2), 4.83 (bs, 2H, NH2), 5.24 (d, J=2.4 Hz, 2H, CH≡CCH2), 7.52-7.62 (m, 3H, PhH), 7.64 (d, J=8.7 Hz, 1H, 7-BenzimidH), 7.65-7.71 (m, 2H, PhH), 7.79 (dd, J=8.7, 1.8 Hz, 1H, 6-BenzimidH), 7.89 (d, J=8.1 Hz, 1H, 5-PhthH), 7.91-7.98 (m, 1H, 6-PhthH), 7.99-8.08 (m, 1H, 7-PhthH), 8.25 (s, 1H, 2-BenzimidH), 8.34 (d, J=1.8 Hz, 4-BenzimidH), 8.72 (d, J=8.1 Hz, 8-PhthH), 9.32 ppm (s, 1H, NH).

후처리

  1. concentrationconcentrated
  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 (1% to 10% methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-8352324f9e144efcb722ac4928913a92
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012217B2

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