Diisopropylethylamine → HCID 68291526, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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	4-Isopropoxy-3-methylbenzoic acid	HCID 59272935	—
Reactant	4-Phenyl-5-oxa-2,9-diazaspiro[5.5]undecan-3-one hydrochloride salt	HCID 68290960	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 68291526	HCID 68291526	40.1%

Reaction Steps

To 4-isopropoxy-3-methyl-benzoic acid (114 mg, 0.59 mmol), 4-phenyl-5-oxa-2,9-diazaspiro[5.5]undecan-3-one hydrochloride salt (166 mg, 0.59 mmol) and HATU (223 mg, 0.59 mmol) in DMF (0.5 mL) was added diisopropylethylamine (228 mg, 307 μL, 1.76 mmol) and the reaction mixture was stirred for 16 hours. The reaction mixture was concentrated in vacuo, diluted with methanol and purified by prep LCMS (1-99% ACN/H2O, 5 mM HCl modifier) to give 3-(4-isopropoxy-3-methyl-benzoyl)-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-9-one (100 mg, 40%) as a yellow foam. ESI-MS m/z calc. 422.2. found 423.5 (M+1)+; Retention time: 1.61 minutes (3 min run).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181273B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-5e83a54d7cfc4e10b866488761598866
Source note	uspto-grants-2015_11