Diisopropylethylamine → HCID 86645949, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	1,3-Benzenedicarboxylic acid, monomethyl ester	HCID 6951279	—
Reactant	3-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol	HCID 86629109	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 86645949	HCID 86645949	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

Monomethyl isophthalate (CAS Reg. No. 1877-71-0, 22 mg), HBTU (CAS Reg. No. 94790-37-1, 62 mg), and N,N-diisopropyl ethyl amine (0.06 ml) were added to a solution of 3-(4-amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (Example 60 step 4, 40 mg) in DMF (2 ml). The mixture was stirred overnight at room temperature, 1 h at 50° C., and then 1 h at 80° C. Additional monomethyl isophthalate (CAS Reg. No. 1877-71-0, 20 mg) and N,N-diisopropyl ethyl amine (0.02 ml) were added. The mixture was purified by prep. HPLC (C18-column, solvent gradient 30-98% CH3CN in 0.1% HCOOH[aq]) to give the title compound (13 mg) as a light yellow foam. MS (m/e)=527.0 [M+H+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08138189B2
Source dataset	uspto-grants-2012_03
ORD ID	ord-c8558586ee734e1e9b7cc025ffa061e2
Source note	uspto-grants-2012_03