Diisopropylethylamine → HCID 68473102, compound

https://huagongshe.com/reaction/2064097

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	tert-butyl N-{[(2S)-piperidin-2-yl]methyl}carbamate	HCID 1501973	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	2-Bromo-5-(4-fluorophenyl)thiazole-4-carboxylic acid	HCID 68474259	—
Solvent	Acetonitrile	HCID 6342	—
Product	HCID 68473102	HCID 68473102	93.2%

Reaction Steps

2-bromo-5-(4-fluoro-phenyl)-thiazole-4-carboxylic acid (1.02 g, 3.38 mmol) was dissolved in acetonitrile (20 ml) followed by the addition of TBTU (1.19 g, 3.72 mmol) and DIPEA (547 mg, 4.22 mmol). Stirring was continued for 30 min. at rt. A solution of (S)-piperidin-2-ylmethyl-carbamic acid tert-butyl ester (725 mg, 3.38 mmol) in acetonitrile (20 ml) was added to the reaction mixture within 10 minutes and stiring was continued at rt for 24 h. The reaction mixture was concentrated under reduced pressure followed by the addition of aq. HCl (0.5 M, 50 ml). Stirring was continued for 30 min. The precipitated product was filtered off, washed with cold water and dried at HV to give the expected product (1.57 g). LC-MS: tR=1.03 min; [M+H]+=500.38.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08288411B2
Source dataset	uspto-grants-2012_10
ORD ID	ord-3914d8327ed0414399d76edccb850f49
Source note	uspto-grants-2012_10