Benzoic Acid → HCID 178518099、化合物

HRID 916248ノート

反応式

HRID 916248 の反応式
[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

参加物

8

反応物 4

HCID 243Benzoic AcidHCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178516941HCID 178516941、化合物

生成物 1

HCID 178518099HCID 178518099、化合物収率 29.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b969d02724404c689cea9cb5037dcb06
出典データセット
uspto-grants-2007_09
特許番号
US07268231B2

反応ノート

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