4-Methylmorpholine → 8-Fluoro-4-(2-hydroxyethyl)-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylamide

HRID 558958ノート

反応式

HRID 558958 の反応式
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]([C:17](=[O:40])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([N:28]3[CH2:34][CH2:33][CH2:32][CH2:31][C:30]4[CH:35]=[CH:36][CH:37]=[CH:38][C:29]3=4)=[O:27])=[CH:22][C:21]=1[CH3:39])[CH2:5][C:6](=[O:16])[N:7]2[CH2:12][C:13](O)=[O:14].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+].[Cl-].[NH4+]>C1COCC1.O>[CH3:39][C:21]1[CH:22]=[C:23]([C:26]([N:28]2[CH2:34][CH2:33][CH2:32][CH2:31][C:30]3[CH:35]=[CH:36][CH:37]=[CH:38][C:29]2=3)=[O:27])[CH:24]=[CH:25][C:20]=1[CH2:19][NH:18][C:17]([N:4]1[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[F:1])[N:7]([CH2:12][CH2:13][OH:14])[C:6](=[O:16])[CH2:5]1)=[O:40]

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 11570214{5-Fluoro-4-[2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylcarbamoyl]-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl}acetic acid

生成物 1

HCID 115482588-Fluoro-4-(2-hydroxyethyl)-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of {5-fluoro-4-[2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylcarbamoyl]-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl}acetic acid from Example 8 (70 mg, 0.13 mmol) in THF (4.0 ml) was added N-methylmorpholine (18 μl, 0.18 mmol. The solution was cooled in an ice/water bath and isobutyl chloroformate (23 μl, 0.18 mmol) was added. The mixture was stirred in the ice/water bath for 1 h, filtered and added to a solution of sodium borohydride (12 mg, 0.32 mmol) in water (1.0 ml) in an ice/water bath. The mixture was allowed to warm to room temperature slowly and stirred at room temperature for 1 h. Saturated ammonium chloride (1 ml) was added and the mixture was evaporated in vacuo. The residue was taken up in water and extracted with chloroform. The organic phase was washed with brine, dried and evaporated in vacuo to give a white solid; yield 56 mg, 81%.

後処理

  1. temperatureThe solution was cooled in an ice/water bath
  2. filtrationfiltered
  3. customthe mixture was evaporated in vacuo
  4. extractionextracted with chloroform
  5. washThe organic phase was washed with brine
  6. customdried
  7. customevaporated in vacuo
  8. customto give a white solid

出典と根拠

ORDレコード
ord-dfb2ed4e855c405e9b4af0af4838eaaa
出典データセット
uspto-grants-2011_11
特許番号
US08063038B2

反応ノート

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