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3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-butyl 3-(1-methyl-2-oxo-2,3,5,6-tetrahydro-1H-[1,2,4]triazino[4,3-a]quinolin-9-ylamino)azetidine-1-carboxylate

HRID 519081
ノート
印刷プレビュー

反応式

HRID 519081 の反応式
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3[N:9]2[CH:12]([CH3:17])[C:13](=[O:16])[NH:14][N:15]=3)=[CH:4][CH:3]=1.O=[C:19]1[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20]1.C([BH3-])#N.[Na+]>CO.CC(O)=O>[CH3:17][CH:12]1[N:9]2[C:10]3[C:5]([CH2:6][CH2:7][C:8]2=[N:15][NH:14][C:13]1=[O:16])=[CH:4][CH:3]=[C:2]([NH:1][CH:19]1[CH2:20][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22]1)[CH:11]=3
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 5003444Sodium cyanoborohydrideHCID 867274479-amino-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one

生成物 1

HCID 86727448tert-butyl 3-(1-methyl-2-oxo-2,3,5,6-tetrahydro-1H-[1,2,4]triazino[4,3-a]quinolin-9-ylamino)azetidine-1-carboxylate収率 34.1%

試薬・触媒・溶媒 2

HCID 176
Acetic Acid
溶媒
HCID 887Methanol溶媒

実験手順

A solution of 9-amino-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one (0.035 g, 0.152 mmol) and tert-butyl 3-oxoazetidine-1-carboxylate (0.078 g, 0.45 mmol) in MeOH (5 mL) and AcOH (0.5 mL) was stirred for 1 h at rt. Sodium cyanoborohydride (0.028 g, 0.456 mmol) was added and the reaction mixture was stirred at ambient temperature overnight. The solution was concentrated in vacuo and the residue was purified by preparative TLC (eluting with 50% EtOAc in petroleum ether) to give tert-butyl 3-(1-methyl-2-oxo-2,3,5,6-tetrahydro-1H-[1,2,4]triazino[4,3-a]quinolin-9-ylamino)azetidine-1-carboxylate (0.020 g, 34%). LC/MS (Table 1, Method 2) Rt=1.104 min; MS m/z: 386 [M+H]+.

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified by preparative TLC (eluting with 50% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-444251dc34c443388c3ef6b98dd7497c
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115151B2

反応ノート

読み込み中…

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