Diisopropylethylamine → HCID 178496869, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Benzyl N-(2-aminoethyl)carbamate	HCID 2794257	—
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	methyl 2-azido-3-(1H-indol-4-yl)acrylate	HCID 72253810	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 178496869	HCID 178496869	206.8%

Reaction Conditions

Temperature	25 °C

Reaction Steps

To compound 1 (18.2 mg, 0.03 mmol) in DMF (2 mL) was added 2 (16 mg, 0.036 mmol) and HATU (14 mg, 0.036 mmol) followed by adding DIPEA (19 uL) and the reaction mixture was stirred for 7 hrs at 25° C. The solvent was removed under vacuo and the product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column), eluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient: 10% acetonitrile in 5 min, 10% to 50% acetonitrile in 15 min, maintaining 50% acetonitrile in 5 min, 50% to 100% acetonitrile in 5 min, to give 3 (15.8 mg, 53%). MS: calcd for C59H58ClN7O9 (M+H) m/z 1044.4 found 1045.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08664407B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-328f34d682ec4ff79a1d6c949efd4406
Source note	uspto-grants-2014_03