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

HRID 913360노트

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HRID 913360 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

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온도
65 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-7052ebfac9d44cbf96dcbcfb94d8211b
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026366B2

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