HCID 178418247, 화합물 → 5-[(8-propan-2-yloxy-1,5-naphthyridin-2-yl)methylidene]-2-(thiophen-2-ylmethylamino)-1,3-thiazol-4-one

HRID 968742노트

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HRID 968742 반응식
[CH:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]=[C:16]3[S:20][C:19]([NH:21][CH2:22][C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[N:18][C:17]3=[O:28])[N:13]=2)[N:8]=[CH:7][C:6]=1C#N)([CH3:3])[CH3:2].C(O[Na])(C)=O.C(OC1C=CN=C2C=1N=C(C=C1SC(NC3CC3C3C=CC=CC=3)=NC1=O)C=C2)(C)C>CC(O)=O>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][N:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH:15]=[C:16]1[S:20][C:19]([NH:21][CH2:22][C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[N:18][C:17]1=[O:28])[CH:11]=[CH:10]2)([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 178418247HCID 178418247, 화합물HCID 178458598HCID 178458598, 화합물HCID 178458710HCID 178458710, 화합물

생성물 1

HCID 1784586025-[(8-propan-2-yloxy-1,5-naphthyridin-2-yl)methylidene]-2-(thiophen-2-ylmethylamino)-1,3-thiazol-4-one수율 45.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

To a mixture of 2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one one (34.0 mg, 0.16 mmol) (see Example 4), AcONa (160 mg, 1.95 mmol), and 8-isopropoxy-[1,5]naphthyridine-2-carbaldehyde (38.9 mg, 0.18 mmol) (see Example 20) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 100° C. (oil bath) for 4.5 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water, acetone and ether to give 5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one as a light brown solid (29.8 mg, 45.4%). HR-ES (+) m/e calcd for C20H18N4O2S2 (M+H)+ 411.0944. found 411.0945.

후처리

  1. temperatureThe reaction mixture was then cooled to r.t.
  2. customtriturated with water
  3. filtrationThe solid was collected by filtration
  4. washwashed with water, acetone and ether

출처 및 근거

ORD 기록
ord-74be7b53c5df494cbe8a414eb0377e3d
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304074B2

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