Ammonium Chloride → HCID 178451066, compound

Participants

Role	Name	HCID	Charge
Reactant	Ammonium Chloride	HCID 25517	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-(Tert-butoxy)-4-oxobutanoic acid	HCID 4139107	—
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	HCID 178508416	HCID 178508416	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 178451066	HCID 178451066	90.5%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of 2-amino-N-[(2,4-dichlorophenyl)methyl]-4-hydroxypyrimidine-5-carboxamide (317 mg), 4-tert-butoxy-4-oxobutanoic acid (529 mg), and N,N-diisopropylethylamine (1.06 mL) in N,N-dimethylformamide (8 mL), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1160 mg) was added at room temperature, and the mixture was stirred at 80° C. for 5 hours. The reaction solution was cooled to room temperature. Then, a saturated aqueous ammonium chloride solution was added thereto, and the mixture was stirred for 10 minutes. The resulting suspension was filtered. The product collected by filtration was washed with water and dried under reduced pressure to obtain the title compound (430 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09206168B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-894b6e1d19634f15b9dcff12faa30329
Source note	uspto-grants-2015_12