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Sodium Carbonate → Ethyl 1-[2-(dimethylamino)ethyl]-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 1047117
ノート
印刷プレビュー

反応式

HRID 1047117 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[CH:7]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22].[CH2:23]([NH:25][C:26](=[O:46])[NH:27][C:28]1[N:33]=[CH:32][C:31](B(O)O)=[C:30]([C:37]2[S:38][CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[N:41]=2)[CH:29]=1)[CH3:24].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][N:14]([CH3:16])[CH2:13][CH2:12][N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:31]3[CH:32]=[N:33][C:28]([NH:27][C:26](=[O:46])[NH:25][CH2:23][CH3:24])=[CH:29][C:30]=3[C:37]3[S:38][CH:39]=[C:40]([C:42]([F:45])([F:43])[F:44])[N:41]=3)=[CH:11][N:10]=2)[C:5](=[O:22])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:7]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

6

反応物 3

HCID 10340Sodium CarbonateHCID 594161896-(3-Ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-ylboronic acid2 回HCID 68747522Ethyl 6-bromo-1-[2-(dimethylamino)ethyl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate2 回

生成物 1

HCID 68748480Ethyl 1-[2-(dimethylamino)ethyl]-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 33.7%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

In a round bottomed flask ethyl 6-bromo-1-[2-(dimethylamino)ethyl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Intermediate 21, 200 mg, 0.54 mmol), 6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-ylboronic acid (Intermediate 9, 288 mg, 0.65 mmol) and sodium carbonate (115 mg, 1.08 mmol) were combined and suspended in dimethylformamide (10 mL) and purged with argon gas for 10 min. Tetrakis (triphenylphosphine) palladium (62 mg, 0.05 mmol) was added under argon atmosphere and the reaction mixture was heated to 90° C. for 2 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 was stirred for 20 min. The obtained solid was filtered and washed with water then dried to afford 110 mg (33%) of ethyl 1-[2-(dimethylamino)ethyl]-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. custompurged with argon gas for 10 min
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationfiltered through celite
  5. additionThe filtrate was poured into water
  6. filtrationThe obtained solid was filtered
  7. washwashed with water
  8. customthen dried

出典と根拠

ORDレコード
ord-0f7f89897cde4d0a836872d4aac1f1b3
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