p-Toluenesulfonic acid monohydrate → 4-(1-methyl-1H-indol-4-ylamino)-2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenylamino)pyrimidine-5-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	p-Toluenesulfonic acid monohydrate	HCID 521998	—
Reactant	4-(2-(Pyrrolidin-1-yl)ethoxy)aniline	HCID 6493749	—
Reactant	2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxamide	HCID 57472013	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	4-(1-methyl-1H-indol-4-ylamino)-2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenylamino)pyrimidine-5-carboxamide	HCID 44594662	45.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxamide (62 mg, 0.15 mmol) in NMP (1 ml) was added 4-(2-(pyrrolidin-1-yl)ethoxy)aniline (31 mg, 0.15 mmol) and p-toluenesulfonic acid hydrate (28 mg, 0.15 mmol). It was heated at 100° C. for 4 h, and was purified by preparative HPLC to give 4-(1-methyl-1H-indol-4-ylamino)-2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenylamino)pyrimidine-5-carboxamide (32 mg). MS found for C26H29N7O2 as (M+H)+ 472.4. UV: λ=216.9, 257.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08501944B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-5b70ef8a7d3746bab0a9cc273c1c6e4d
Source note	uspto-grants-2013_08