Diisopropylethylamine → HCID 59554867, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one	HCID 88638	—
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	HCID 59555338	HCID 59555338	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Acetonitrile	HCID 6342	—
Product	HCID 59554867	HCID 59554867	—

Reaction Steps

To a solution of 2-(3-isopropyl-4-oxo-2-phenylthiazolidin-5-yl)acetic acid (0.2 mmol, 56 mg), 1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one (0.15 mmol, 33 mg) and DIPEA (0.375 mmol, 65.3 μl) in 4:1 CH3CN:DMF (0.5 ml) was added HATU (0.18 mmol, 68 mg) and the reaction mixture was stirred at room temperature for 16 h. Purification by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) gave the title compound. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=493.5; tR=3.1. 1H NMR (400 MHz, CDCl3) δ 7.31-7.25 (m, 5H), 7.14-7.10 (m, 1H), 7.05 (s, 1H), 7.00 (m, 1H), 6.93-6.89 (m, 1H), 6.62 (d, J=7.8 Hz, 1H), 5.56 (m, 1H), 4.72 (m, 1H), 4.47-4.41 (m, 2H), 4.27-4.19 (m, 2H), 4.02-3.96 (m, 1H), 3.87 (m, 1H), 3.36-3.29 (m, 1H), 3.13-3.10 (m, 1H), 2.70 (m, 2H), 1.70-1.60 (m, 3H), 1.20 (dd, J=2.0, 6.9 Hz, 3H), 0.94 (m, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08163737B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-1073915087ab4f84bbc197994b3fc97c
Source note	uspto-grants-2012_04