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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
Notes
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Reaction equation

HRID 1711118 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 59457671HCID 59457671, compound

Product 1

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

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolvent
HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-006b9b5fc7f04d7fab82f6d859d810db
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07790729B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes