Diisopropylethylamine → (S)-tert-butyl 4-(2-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-(2-(1-(2-phenylacetyl)pyrrolidin-2-yl)-1H-imidazol-4-yl)phenylcarbamoyl)phenylthio)phenylcarbamate

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	4-(4-tert-Butoxycarbonylamino-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid	HCID 59376892	—
Reactant	HCID 178507416	HCID 178507416	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Water	HCID 962	—
Product	(S)-tert-butyl 4-(2-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-(2-(1-(2-phenylacetyl)pyrrolidin-2-yl)-1H-imidazol-4-yl)phenylcarbamoyl)phenylthio)phenylcarbamate	HCID 136158805	36%

Reaction Steps

To a solution of the Product from Example 1E (0.16 g, 0.30 mmol) and HATU (0.12 g, 0.316 mmol) in DMSO (5 mL) was added diisopropylethylamine (0.184 mL, 1.05 mmol) followed by the Product from Example 1J (0.115 g, 0.33 mmol). The solution was stirred at ambient temperature for 18 hours, then diluted with water and the crude product was filtered off an purified by combi-flash 12 g column, eluting with 0-10% Methanol in dichloromethane to give a solid (0.092 g, 36%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08541424B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-dcb6d69ae0e444d79d1a83f9f5b04b29
Source note	uspto-grants-2013_09