Diisopropylethylamine → tert-butyl 7-({(1S)-1-[4-(methoxycarbonyl)phenyl]ethyl}carbamoyl)indoline-1-carboxylate

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	N-Boc-indoline-7-carboxylic acid	HCID 14977845	—
Reactant	[(1S)-1-(4-methoxycarbonylphenyl)ethyl]azanium chloride	HCID 161770108	—
Solvent	Acetonitrile	HCID 6342	—
Product	tert-butyl 7-({(1S)-1-[4-(methoxycarbonyl)phenyl]ethyl}carbamoyl)indoline-1-carboxylate	HCID 58125255	—

Reaction Steps

1-(tert-butoxycarbonyl)indoline-7-carboxylic acid (0.5 g, 1.9 mmol), HATU (795 mg, 2.09 mmol) and (1S)-1-[4-(methoxycarbonyl)phenyl]ethanaminium chloride (511 mg, 2.85 mmol) were added to acetonitrile (12.7 ml). The solution was cooled in an ice bath and DIPEA (993 ul, 5.7 mmol) was added. The ice bath was removed and the mixture stirred for 2 hours at RT. The solvent was removed and the crude mixture purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): δ 8.40 (d, 1H), 7.90 (d, 2H), 7.55 (d, 2H), 7.30 (d, 1H), 7.25 (d, 1H), 7.00 (t, 1H), 5.10 (m, 1H), 4.00 (m, 2H), 3.85 (s, 3H), 3.05 (m, 2H), 1.45 (d, 3H), 1.40 (s, 9H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07705035B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-80c6e4df44d1416a96c6a608a50359a6
Source note	uspto-grants-2010_04