Benzoic Acid → HCID 178518099, 화합물

HRID 916248노트

반응식

HRID 916248 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.[N:17]1[C:26]2[C:21](=[N:22][C:23]([CH:27]=O)=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1.CN(C=O)C.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:27][C:23]2[CH:24]=[CH:25][C:26]3[C:21](=[CH:20][CH:19]=[CH:18][N:17]=3)[N:22]=2)[C:10](=[O:12])[N:11]=1

참가 물질

8

반응물 4

HCID 243Benzoic AcidHCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178516941HCID 178516941, 화합물

생성물 1

HCID 178518099HCID 178518099, 화합물수율 29.2%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매2회HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

To a suspension of 2-(3-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 mg, 0.16 mmol), and 1,5-naphthyridine-6-carboxaldehyde (31.6 mg, 0.20 mmol) in toluene (1 mL) in a microwave tube were added benzoic acid (2.0 mg, 0.02 mmol) and piperidine (1.7 uM, 0.02 mmol). The reaction mixture was heated to 130° C. with microwave for 10 min. The reaction mixture was then cooled to r.t. and diluted with toluene. The solid was collected by filtration and washed with toluene, MeOH and ether to give a brown solid: 32.6 mg (51.1%), which was dissolved in 0.5 mL hot DMF and diluted with water. The precipitates were collected and washed with water, acetone and ether, dried to give 2-(3-chloro-4-fluoro-benzylamino)-5-[1,5]naphthyridin-2-ylmethylene-thiazol-4-one as a light brown solid (18.6 mg, 29.2%). HR-ES (+) m/e calcd. for C19H12ClFN4OS: (M+H)+ 399.0477. Found: 399.0477.

후처리

  1. temperatureThe reaction mixture was then cooled to r.t.
  2. filtrationThe solid was collected by filtration
  3. washwashed with toluene, MeOH and ether
  4. customto give a brown solid
  5. customThe precipitates were collected
  6. washwashed with water, acetone and ether
  7. customdried

출처 및 근거

ORD 기록
ord-b969d02724404c689cea9cb5037dcb06
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268231B2

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