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Ammonium Chloride → tert-Butyl 4-(4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)benzyl)piperazine-1-carboxylate

HRID 1711118
ノート
印刷プレビュー

反応式

HRID 1711118 の反応式
[F:1][C:2]1[CH:37]=[C:36]([N+:38]([O-])=O)[CH:35]=[CH:34][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:33]=[CH:32][C:17]([CH2:18][N:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)=[CH:16][CH:15]=3)[S:13][C:6]=12.[NH4+].[Cl-]>O.CCO.CO.[Fe]>[NH2:38][C:36]1[CH:35]=[CH:34][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[CH:33]=[CH:32][C:17]([CH2:18][N:19]5[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]5)=[CH:16][CH:15]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:37]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 25517Ammonium ChlorideHCID 59457671HCID 59457671、化合物

生成物 1

HCID 59457718tert-Butyl 4-(4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)benzyl)piperazine-1-carboxylate収率 83%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 702Ethanol溶媒
HCID 887
Methanol
溶媒
HCID 962Water溶媒

実験手順

Compound 453 (5.4 g, 9.56 mmol), iron powder (1.602 g, 28.69 mmol) and NH4Cl (0.78 g, 14.34 mmol) were placed in a mixture of H2O (24mL) and EtOH (48 mL). The reaction mixture was heated to reflux for 5 h. It was then cooled to RT, diluted with MeOH and filtered through a pad of celite. The filtrate was concentrated to dryness and the residue was dissolved in dichloromethane, washed with aqueous NaHCO3 and brine, dried over Na2SO4, and filtered. The filtrate was concentrated to dryness to give compound 454 as white solid (4.2 g, 83% yield). LCMS: 535 (M+H)+.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. filtrationfiltered through a pad of celite
  4. concentrationThe filtrate was concentrated to dryness
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washwashed with aqueous NaHCO3 and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated to dryness

出典と根拠

ORDレコード
ord-006b9b5fc7f04d7fab82f6d859d810db
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07790729B2

反応ノート

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