1,2-Dichloroethane → [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(3R)-3,4-dimethyl-1-piperazinyl]-5-fluoro-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	HOAt	HCID 181649	—
Reactant	(R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acid	HCID 21305218	—
Reactant	HCID 66936099	HCID 66936099	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(3R)-3,4-dimethyl-1-piperazinyl]-5-fluoro-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide	HCID 86636944	50.5%

Reaction Steps

(2R)-3-Cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.079 g, 0.30 mmol), 4-[(3R)-3,4-dimethyl-1-piperazinyl]-5-fluoro-6-hydrazino-2-methylpyrimidine (0.079 g, 0.31 mmol), NMM (0.10 mL, 0.90 mmol), HOAt (0.042 g, 0.31 mmol), and EDC (0.059 g, 0.31 mmol) were dissolved in DMF (4 mL) and treated in a manner similar to General Procedure A, Part B, to provide [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(3R)-3,4-dimethyl-1-piperazinyl]-5-fluoro-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.082 g, 49%). LCMS: (M+H)+=542.7.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07893056B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-af78d19cf8aa4803b11bd85d6278a29b
Source note	uspto-grants-2011_02