Chlorosuccinimide → 8-((2-amino-2,4-dimethylpentyl)oxy)-9-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398394ノート

反応式

HRID 1398394 の反応式
C(OC(=O)[NH:7][C:8]([CH3:32])([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:23]3[C:18](=[C:19]([CH3:24])[N:20]=[CH:21][CH:22]=3)[C:17](=[O:25])[N:16]([CH3:26])[C:15]=2[CH:27]=1)(C)(C)C.C1C(=O)N([Cl:41])C(=O)C1>C(#N)C>[NH2:7][C:8]([CH3:32])([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:9][O:10][C:11]1[C:12]([Cl:41])=[CH:13][C:14]2[C:23]3[C:18](=[C:19]([CH3:24])[N:20]=[CH:21][CH:22]=3)[C:17](=[O:25])[N:16]([CH3:26])[C:15]=2[CH:27]=1

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 89957266Tert-butyl(1-((4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-2,4-dimethylpentan-2-yl)carbamate

生成物 1

HCID 732140208-((2-amino-2,4-dimethylpentyl)oxy)-9-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one収率 13.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To the stirred solution of 8-((2-amino-2,4-dimethylpentyl)oxy)-4,6 dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (Prepared in Example 32, Part B) (0.08 g, 0.226 mmol) in acetonitrile (5 mL) was added NCS (0.030 g, 0.226 mmol)) at RT and the reaction mixture was stirred for 2 h. The mixture was then evaporated to dryness. The residue was purified by reverse phase HPLC (0.1% TFA in water/AcCN) to afford 8-((2-amino-2,4-dimethylpentyl)oxy)-9-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (12 mg, 0.030 mmol, 13% yield). LC/MS (ESI) m/e 388.0 [(M+H)+, calcd for C21H27ClN3O2, 388.2] as an off-white solid. LC/MS retention time (method C): tR=2.13 min. HPLC retention time (method A): tR=8.97 min; HPLC retention time (method B): tR=10.16 min. 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.99-1.02 (m, 6H), 1.30 (s, 3H), 1.54-1.66 (m, 2H), 1.84-1.90 (m, 1H), 3.05 (s, 1H), 3.73 (s, 1H), 4.04 (q, J=23.20 Hz, 2H), 7.03 (s, 1H), 8.06 (d, J=6.00 Hz, 1H), 8.39 (s, 1H), 8.54 (d, J=6.00 Hz, 1H).

後処理

  1. customThe mixture was then evaporated to dryness
  2. customThe residue was purified by reverse phase HPLC (0.1% TFA in water/AcCN)

出典と根拠

ORDレコード
ord-99323c73ed73492e9f9ae7e807da7b5a
出典データセット
uspto-grants-2014_12
特許番号
US08901305B2

反応ノート

読み込み中…