Hydrochloric Acid → 3-[(1S,2S)-2-aminocyclohexyl]-6-[(6-chloropyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one

HRID 1042305ノート

反応式

HRID 1042305 の反応式
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[N:14]1[C:23](=[O:24])[C:22]2[C:17](=[C:18]3[CH:36]=[CH:35][CH:34]=[CH:33][C:19]3=[C:20]([CH2:25][C:26]3[CH:27]=[N:28][C:29]([Cl:32])=[CH:30][CH:31]=3)[CH:21]=2)[N:16]=[CH:15]1)(C)(C)C.Cl>CO>[NH2:7][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[N:14]1[C:23](=[O:24])[C:22]2[C:17](=[C:18]3[CH:36]=[CH:35][CH:34]=[CH:33][C:19]3=[C:20]([CH2:25][C:26]3[CH:27]=[N:28][C:29]([Cl:32])=[CH:30][CH:31]=3)[CH:21]=2)[N:16]=[CH:15]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 46208971tert-butyl{(1S,2S)-2-[6-[(6-chloropyridin-3-yl)methyl]-4-oxobenzo[h]quinazolin-3(4H)-yl]cyclohexyl}carbamate

生成物 1

HCID 462089723-[(1S,2S)-2-aminocyclohexyl]-6-[(6-chloropyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of tert-butyl{(1S,2S)-2-[6-[(6-chloropyridin-3-yl)methyl]-4-oxobenzo[h]quinazolin-3(4H)-yl]cyclohexyl}carbamate (0.080 g, 0.15 mmol) in 2 mL of methanol was added hydrochloric acid (0.15 mL, 6 N aqueous, 0.92 mmol). The reaction was heated at 60° C. for 2 h, cooled to ambient temperature and concentrated in vacuo. The residue was concentrated twice with toluene. The residue was purified via preparative reverse phase HPLC to provide 3-[(1S,2S)-2-aminocyclohexyl]-6-[(6-chloropyridin-3-yl)methyl]benzo[h]quinazolin-4(3H)-one that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 419.0 for [M+H]+: 1H NMR (400 MHz, d6-DMSO) δ 9.10-9.08 (m, 1H), 8.56 (br s, 1H), 8.27 (s, 1H), 8.14-8.12 (m, 1H), 8.04 (s, 1H), 7.80-7.75 (m, 3H), 7.43-7.36 (m, 1H), 4.60 (s, 2H), 2.31-2.24 (m, 2H), 2.12-1.94 (m, 4H), 1.70-1.56 (m, 4H).

後処理

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. concentrationThe residue was concentrated twice with toluene
  4. customThe residue was purified via preparative reverse phase HPLC

出典と根拠

ORDレコード
ord-6ad7abbf9fc64da5b2aa7015491986bd
出典データセット
uspto-grants-2013_10
特許番号
US08557832B2

反応ノート

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