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4-Fluorobenzylamine → HCID 178429626, compound

HRID 23630
Notes
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Reaction equation

HRID 23630 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]2[C:13]([CH3:18])=[C:14]([CH2:16][OH:17])[S:15][C:3]=12.[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>Cl>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:8]([C:7]2[C:2]([OH:1])=[C:3]3[S:15][C:14]([CH2:16][OH:17])=[C:13]([CH3:18])[C:4]3=[N:5][CH:6]=2)=[O:10])=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 178469552HCID 178469552, compound

Product 1

HCID 178429626HCID 178429626, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 140 mg (0.52 mmol) ethyl 7-hydroxy-2-(hydroxymethyl)-3-methylthieno[3,2-b]pyridine-6-carboxylate in 1.28 mL (11.2 mmol) 4-fluorobenzylamine was heated to 80° C. for 24 hours. The mixture was then cooled to room temperature and added to 10 mL of 1N HCl and then cooled in the refrigerator for three hours. The resulting mixture was then filtered and the obtained solid was washed with 1N HCl several times (50 mL total volume) and dried in a vacuum oven at 60° C. over night to provide 154 mg of the title compound as a tan solid.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. temperaturecooled in the refrigerator for three hours
  3. filtrationThe resulting mixture was then filtered
  4. washthe obtained solid was washed with 1N HCl several times (50 mL total volume)
  5. customdried in a vacuum oven at 60° C. over night

Sources & evidence

ORD record
ord-bc944c46c3124ec2806eac8d44ed2373
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06852731B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes