Propargyl bromide → 2-Ethyl-7-[(prop-2-ynyl)oxy]thiazolo[4,5-c]quinolin-4-amine

HRID 913360ノート

反応式

HRID 913360 の反応式
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:15][CH3:16])[S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:17])=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](Br)[C:25]#[CH:26]>CN(C=O)C.C1(C)C=CC=CC=1>[CH2:15]([C:13]1[S:14][C:10]2[C:9]3[CH:8]=[CH:7][C:6]([O:17][CH2:26][C:25]#[CH:24])=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:16]

参加物

6

反応物 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 1363391164-Amino-2-ethylthiazolo[4,5-c]quinolin-7-ol

生成物 1

HCID 860908572-Ethyl-7-[(prop-2-ynyl)oxy]thiazolo[4,5-c]quinolin-4-amine

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

To a stirred solution (pale orange) of 4-amino-2-ethylthiazolo[4,5-c]quinolin-7-ol (0.24 g, 1.0 mmol) was dissolved in anhydrous DMF (5 mL) was added cesium carbonate (3.0 eq., 1.0 g, 3.0 mmol) and 1.1 eq. of an 80% solution of propargyl bromide in toluene (0.16 g). The mixture was heated to 65° C. and maintained overnight. The reaction was quenched by slowly adding the reaction mixture to 10 volumes of water (50 mL). The resulting solid was collected by vacuum filtration, rinsed with acetonitrile and air dried, to provide 0.22 g of 2-ethyl-7-[(prop-2-ynyl)oxy]thiazolo[4,5-c]quinolin-4-amine as a pale-peach colored crystalline solid. MS (ACPI) m/z=284 (M+H)+.

後処理

  1. temperaturemaintained overnight
  2. customThe reaction was quenched
  3. additionby slowly adding the reaction mixture to 10 volumes of water (50 mL)
  4. filtrationThe resulting solid was collected by vacuum filtration
  5. washrinsed with acetonitrile and air
  6. customdried

出典と根拠

ORDレコード
ord-7052ebfac9d44cbf96dcbcfb94d8211b
出典データセット
uspto-grants-2011_09
特許番号
US08026366B2

反応ノート

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