HCID 178418247, 화합물 → HCID 178458599, 화합물

HRID 968743노트

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HRID 968743 반응식
[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:12][C:13]2[N:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][C:17](C#N)=[C:16]3[O:25][CH:26]([CH3:28])[CH3:27])[C:9](=[O:11])[N:10]=1.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>[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([O:25][CH:26]([CH3:28])[CH3:27])[CH:17]=[CH:18][N:19]=3)[N:14]=2)[C:9](=[O:11])[N:10]=1

참가 물질

5

반응물 3

HCID 178418247HCID 178418247, 화합물HCID 178458598HCID 178458598, 화합물HCID 178458708HCID 178458708, 화합물

생성물 1

HCID 178458599HCID 178458599, 화합물수율 44.7%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

To a mixture of 2-(2-chloro-benzylamino)-thiazol-4-one (38.5 mg, 0.16 mmol) (see Example 2), AcONa (160 mg, 1.95 mmol), molecular sieves, 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 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 collected by filtration and washed with water, acetone and ether to give 2-(2-chloro-benzylamino)-5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-thiazol-4-one as a brown solid (31.4 mg, 44.7%). HR-ES (+) m/e calcd for C22H19ClN4O2S (M+H)+ 439.0990. found 439.0987.

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. filtrationThe solid was collected by filtration
  6. washwashed with water, acetone and ether

출처 및 근거

ORD 기록
ord-e114255a5b4449fbb2cc310e948eb5bf
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304074B2

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