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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
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HRID 1711118 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

HCID 25517Ammonium ChlorideHCID 59457671HCID 59457671, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 23925Iron촉매HCID 702Ethanol용매
HCID 887
Methanol
용매
HCID 962Water용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-006b9b5fc7f04d7fab82f6d859d810db
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07790729B2

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