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Sodium Carbonate → Ethyl 1-cyclopropyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047113
ノート
印刷プレビュー

反応式

HRID 1047113 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH:12]1[CH2:14][CH2:13]1)[CH:7]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2=[O:20].[CH2:21]([NH:23][C:24](=[O:44])[NH:25][C:26]1[N:31]=[CH:30][C:29](B(O)O)=[C:28]([C:35]2[S:36][CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[N:39]=2)[CH:27]=1)[CH3:22].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH:12]1([N:8]2[C:9]3[C:4](=[CH:3][C:2]([C:29]4[CH:30]=[N:31][C:26]([NH:25][C:24](=[O:44])[NH:23][CH2:21][CH3:22])=[CH:27][C:28]=4[C:35]4[S:36][CH:37]=[C:38]([C:40]([F:43])([F:41])[F:42])[N:39]=4)=[CH:11][N:10]=3)[C:5](=[O:20])[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7]2)[CH2:14][CH2:13]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 594161896-(3-Ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-ylboronic acid2 回HCID 68750837Ethyl 6-bromo-1-cyclopropyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate2 回

生成物 1

HCID 68747362Ethyl 1-cyclopropyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate収率 20.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

In a round bottomed flask, ethyl 6-bromo-1-cyclopropyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Intermediate 16, 200 mg, 0.59 mmol), 6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-ylboronic acid (Intermediate 9, 367 mg, 0.83 mmol) and sodium carbonate (125 mg, 1.18 mmol) were combined and suspended in dimethylformamide (10 mL). Argon gas was purged through the above suspension for 15 min. At the end of this period, tetrakis (triphenylphosphine) palladium (68 mg, 0.05 mM) was added under argon atmosphere and the reaction mixture was heated to 40° C. for 6 h. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered through celite. The filtrate was poured into water and stirred for 30 min to obtain a solid which was filtered and washed with water and dried to afford 70 mg (20%) of ethyl 1-cyclopropyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate.

後処理

  1. customArgon gas was purged through the above suspension for 15 min
  2. additionAt the end of this period, tetrakis (triphenylphosphine) palladium (68 mg, 0.05 mM) was added under argon atmosphere
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled to room temperature
  5. filtrationfiltered through celite
  6. additionThe filtrate was poured into water
  7. customto obtain a solid which
  8. filtrationwas filtered
  9. washwashed with water
  10. customdried

出典と根拠

ORDレコード
ord-ba5cb085782e424890b31ee877bd385f
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08569484B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート