Triethylamine → 4-bromo-N-(1-{[(4S)-3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl}-4-piperidinyl)benzamide

HRID 15326

反応式

HRID 15326 の反応式
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]2[C:13]3=[C:14]([F:22])[CH:15]=[N:16][C:17]4[CH:18]=[CH:19][C:20](=[O:21])[N:11]([C:12]=43)[CH2:10]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[Br:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][C@@H:9]3[C:13]4=[C:14]([F:22])[CH:15]=[N:16][C:17]5[CH:18]=[CH:19][C:20](=[O:21])[N:11]([C:12]=54)[CH2:10]3)[CH2:4][CH2:3]2)=[O:36])=[CH:33][CH:32]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 686864184-[(4-Amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one2 回

生成物 1

HCID 577074654-bromo-N-(1-{[(4S)-3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl}-4-piperidinyl)benzamide収率 87%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Enantiomer 2 (200 mg, 0.664 mmol) in dichloromethane (5 ml) was treated with triethylamine (0.139 ml, 1 mmol), ice-cooled under argon and treated with 4-bromobenzoyl chloride (150 mg, 0.682 mmol). The solution was shaken with excess aqueous sodium bicarbonate solution, separated and the aqueous re-extracted twice with 15% methanol/dichloromethane. The combined organic extracts were dried and evaporated and the residue chromatographed using dichloromethane/methanol/0.88 ammonia 96:4:0.4 to give 4-bromo-N-(1-{[(4S)-3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl}-4-piperidinyl)benzamide (280 mg, 87%).

後処理

  1. temperaturecooled under argon
  2. customseparated
  3. extractionthe aqueous re-extracted twice with 15% methanol/dichloromethane
  4. customThe combined organic extracts were dried
  5. customevaporated
  6. customthe residue chromatographed

出典と根拠

ORDレコード
ord-41f14deadf084fcd846af4462c10776c
出典データセット
uspto-grants-2010_06
特許番号
US07732461B2

関連ノート

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