HCID 178418247, 화합물 → HCID 178458601, 화합물

HRID 968744노트

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HRID 968744 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:5][NH:6][C:7]1[S:8][C:9](=[CH:13][C:14]2[N:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[CH:19][C:18](C#N)=[CH:17]3)[C:10](=[O:12])[N:11]=1.C(O[Na])(C)=O.[CH:35]([O:38]C1C=CN=C2C=1N=C(C=C1SC(NC3CC3C3C=CC=CC=3)=NC1=O)C=C2)([CH3:37])[CH3:36]>CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:5][NH:6][C:7]1[S:8][C:9](=[CH:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[C:17]([O:38][CH:35]([CH3:37])[CH3:36])[CH:18]=[CH:19][N:20]=3)[N:15]=2)[C:10](=[O:12])[N:11]=1

참가 물질

5

반응물 3

HCID 178418247HCID 178418247, 화합물HCID 178458598HCID 178458598, 화합물HCID 178510296HCID 178510296, 화합물

생성물 1

HCID 178458601HCID 178458601, 화합물수율 86.9%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

To a mixture of 2-(3-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 mg, 0.16 mmol) (see Example 19), 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 2 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 2-(3-chloro-4-fluoro-benzylamino)-5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-thiazol-4-one as a light brown solid (63.5 mg, 86.9%). HR-ES (+) m/e calcd for C22H18FClN4O2S (M+H)+ 457.0896. found 457.0897.

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-21219c33423c4b9a85889191be17a1ed
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304074B2

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