Hexane → Prop-1-en-2-yl (4-chloro-5-(1-ethyl-7-((4-methoxybenzyl)(methyl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)carbamate

HRID 1257166ノート

反応式

HRID 1257166 の反応式
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]([CH3:31])[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:22]4[CH:27]=[C:26]([NH2:28])[C:25]([F:29])=[CH:24][C:23]=4[Cl:30])[C:15](=[O:21])[N:16]3[CH2:19][CH3:20])=[CH:11][N:10]=2)=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].Cl[C:40]([O:42][C:43]([CH3:45])=[CH2:44])=[O:41].CCCCCC>CCOC(C)=O>[Cl:30][C:23]1[C:22]([C:14]2[C:15](=[O:21])[N:16]([CH2:19][CH3:20])[C:17]3[C:12]([CH:13]=2)=[CH:11][N:10]=[C:9]([N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:33][CH:32]=2)[CH3:31])[CH:18]=3)=[CH:27][C:26]([NH:28][C:40](=[O:41])[O:42][C:43]([CH3:45])=[CH2:44])=[C:25]([F:29])[CH:24]=1

参加物

6

反応物 4

HCID 8058HexaneHCID 93846Isopropenyl chloroformateHCID 516892Sodium BicarbonateHCID 896061707-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-1,6-naphthyridin-2(1H)-one

生成物 1

HCID 89611459Prop-1-en-2-yl (4-chloro-5-(1-ethyl-7-((4-methoxybenzyl)(methyl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)carbamate収率 99%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A bi-phasic mixture of Example A4 (1.00 g, 2.142 mmol) in EtOAc (25 mL) and satd. NaHCO3 (25 mL) was treated with isopropenyl chloroformate (516 mg, 4.28 mmol) and stirred vigorously at RT for 3 h. Hexane (10 mL) was added and the resulting solid collected via filtration and dried. The layers of the filtrate were separated, the organic layer washed with brine, dried over Na2SO4, concentrated to dryness and combined with the above-isolated solid to afford prop-1-en-2-yl (4-chloro-5-(1-ethyl-7-((4-methoxybenzyl)(methyl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)carbamate (1.168 g, 98% yield). MS (ESI) m/z: 551.2 [M+H]+.

後処理

  1. filtrationthe resulting solid collected via filtration
  2. customdried
  3. customThe layers of the filtrate were separated
  4. washthe organic layer washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-da4aca5deb844add8ccaa470b2e7b8fa
出典データセット
uspto-grants-2013_06
特許番号
US08461179B1

反応ノート

読み込み中…