Diisopropylethylamine → 2-(4-{(E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acryloylamino}-butoxy)-6-benzyloxybenzoic Acid Methyl Ester

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	2-(4-Aminobutoxy)-6-benzyloxybenzoic Acid Methyl Ester	HCID 68429372	—
Reactant	(E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic Acid	HCID 68840076	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(4-{(E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acryloylamino}-butoxy)-6-benzyloxybenzoic Acid Methyl Ester	HCID 68837876	—

Reaction Steps

To a solution of (E)-2-acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic acid (260 mg, 0.58 mmol) in DMF (10 mL) is added diisopropylethylamine (0.11 mL, 0.64 mmol) and HATU (243 mg, 0.64 mmol). The mixture is stirred at RT for 10 min then a solution of 2-(4-aminobutoxy)-6-benzyloxybenzoic acid methyl ester (Example 110, step C) (286 mg, 0.87 mmol) in DMF (1 mL) is added and stirring is continued for 18 h. The solvent is removed under reduced pressure to give the title compound which is used directly in the next step.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08084448B2
Source dataset	uspto-grants-2011_12
ORD ID	ord-a17a1946203e4388893dfd76512db59d
Source note	uspto-grants-2011_12