8-Isopropoxy-[1,5]naphthyridine-2-carbaldehyde → HCID 178458598, 화합물

HRID 968734노트

반응식

HRID 968734 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][CH:22]4[CH2:24][CH:23]4[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:18][C:17]3=[O:31])[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=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][CH:22]3[CH2:24][CH:23]3[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:18][C:17]1=[O:31])[CH:11]=[CH:10]2)([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 587243028-Isopropoxy-[1,5]naphthyridine-2-carbaldehydeHCID 178418247HCID 178418247, 화합물HCID 178458707HCID 178458707, 화합물

생성물 1

HCID 178458598HCID 178458598, 화합물수율 73.7%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

To a mixture of 2-(trans)-phenylcyclopylamino-thiazol-4-one (76.0 mg, 0.32 mmol) (see Example 3) AcONa (160 mg, 1.95 mmol), and 8-isopropoxy-[1,5]naphthyridine-2-carbaldehyde (77.8 mg, 0.36 mmol) (prepared as described below) in a sealed tube was added AcOH (0.4 mL). The reaction mixture was heated to 100° C. (oil bath) for 4 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-(2-phenyl-cyclopropylamino)-thiazol-4-one as a yellowish solid (101.5 mg, 73.7%). HR-ES (+) m/e calcd for C24H22N4O2S (M+H)+ 431.1536. found 431.1537.

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-22ac91824a834d7784e61cd90de76eab
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304074B2

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