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6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → 6-[[2-[(3-methylthiophen-2-yl)methylamino]-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-propan-2-yloxy-1,5-naphthyridine-3-carbonitrile

HRID 968718
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HRID 968718 반응식
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][NH:8][C:9]1[S:10][CH2:11][C:12](=[O:14])[N:13]=1.C(O[Na])(C)=O.[CH:20]([C:22]1[N:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][C:26]([C:32]#[N:33])=[C:25]2[O:34][CH:35]([CH3:37])[CH3:36])=O>CC(O)=O>[CH:35]([O:34][C:25]1[C:24]2[C:29](=[CH:30][CH:31]=[C:22]([CH:20]=[C:11]3[S:10][C:9]([NH:8][CH2:7][C:3]4[S:4][CH:5]=[CH:6][C:2]=4[CH3:1])=[N:13][C:12]3=[O:14])[N:23]=2)[N:28]=[CH:27][C:26]=1[C:32]#[N:33])([CH3:37])[CH3:36]
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참가 물질

5

반응물 3

HCID 587243116-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrileHCID 178418247HCID 178418247, 화합물HCID 178429647HCID 178429647, 화합물

생성물 1

HCID 1784296466-[[2-[(3-methylthiophen-2-yl)methylamino]-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-propan-2-yloxy-1,5-naphthyridine-3-carbonitrile수율 32.4%

시약·촉매·용매 1

HCID 176
Acetic Acid
용매

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온도
80 °C

실험 절차

To a mixture of 2-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one (36.2 mg, 0.16 mmol) (prepared as described below), AcONa (160 mg, 1.95 mmol), and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (50.2 mg, 0.21 mmol) (see Example 1) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 80° C. (oil bath) for 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. The solid was then suspended in AcOEt (20 mL) and filtered through a glass. The solid was washed with AcOEt and dried to give 4-isopropoxy-6-{2-[(3-methyl-thiophen-2-ylmethyl)-amino]-4-oxo-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a light brown solid (22.6 mg, 32.4%). HR-ES (+) m/e calcd for C22H19N5O2S2 (M+H)+ 450.1053. found 450.1051.

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
  5. filtrationfiltered through a glass
  6. washThe solid was washed with AcOEt
  7. customdried

출처 및 근거

ORD 기록
ord-7348c88cce3b4c8d9d1a6d5e863996a1
출처 데이터셋
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07304074B2

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