HCID 178418247, 화합물 → HCID 178510296, 화합물

HRID 968733노트

반응식

HRID 968733 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][C:7]1[S:8][CH2:9][C:10](=[O:12])[N:11]=1.C(O[Na])(C)=O.O=C1C(=[CH:28][C:29]2[N:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][C:33]([C:39]#[N:40])=[CH:32]3)SC(NCC2SC=CC=2)=N1>CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][C:7]1[S:8][C:9](=[CH:28][C:29]2[N:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][C:33]([C:39]#[N:40])=[CH:32]3)[C:10](=[O:12])[N:11]=1

참가 물질

5

반응물 3

HCID 178418247HCID 178418247, 화합물HCID 178510297HCID 178510297, 화합물HCID 178516941HCID 178516941, 화합물

생성물 1

HCID 178510296HCID 178510296, 화합물수율 45.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
120 °C

실험 절차

To a mixture of 2-(3-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 mg, 0.16 mmol) (prepared as described below) AcONa (160 mg, 1.95 mmol), and 6-formyl-[1,5]naphthyridine-3-carbonitrile (33.6 mg, 0.18 mmol) (see Example 11) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 120° C. (oil bath) for 3 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water, AcOEt and ether to give 6-[2-(3-chloro-4-fluoro-benzylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-[1,5]naphthyridine-3-carbonitrile as a light brown solid (30.6 mg, 45.1%). HR-ES (+) m/e calcd for C20H11FClN5OS (M+H)+ 424.0430. found 424.0431.

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, AcOEt and ether

출처 및 근거

ORD 기록
ord-72531deee3564b4c8e28ef1ce1d2bbc0
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304074B2

반응 노트

불러오는 중…