Triethylamine → (5-Ethylthiophen-3-yl)(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	5-Ethylthiophene-3-carboxylic acid	HCID 3561548	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)phenyl)ethanol	HCID 57989385	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(5-Ethylthiophen-3-yl)(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone	HCID 57989056	—

Reaction Steps

HATU (0.209 g) was added to a stirred solution of 5-ethylthiophene-3-carboxylic acid (0.086 g), 2-(3-(1-oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)phenyl)ethanol (example 82, step a) (0.160 g), and triethylamine (0.3 mL) in DMF (2 mL). After 1 h, the reaction mixture was diluted with ethyl acetate (25 mL) and washed with brine (2×25 mL). The ethyl acetate layer was evaporated in vacuo. Purification by silica gel chromatography eluting with 10:1, ethyl acetate:triethylamine gave the subtitled compound as a gum. Yield 0.18 g.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08629271B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-19581713da8040d09f60122e0e33abb3
Source note	uspto-grants-2014_01