4-Fluorobenzylamine → HCID 178429626, compound

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

Participants

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

temperatureThe mixture was then cooled to room temperature
temperaturecooled in the refrigerator for three hours
filtrationThe resulting mixture was then filtered
washthe obtained solid was washed with 1N HCl several times (50 mL total volume)
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

Linked notes

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