HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → ((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-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 | 5-Fluoro-4-hydrazino-2-methyl-6-(1-pyrrolidinyl)pyrimidine | HCID 66936020 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | ((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide | HCID 86636916 | 55% |
Reaction Steps
5-Fluoro-4-hydrazino-2-methyl-6-(1-pyrrolidinyl)pyrimidine (69 mg, 0.33 mmol), (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (110 mg, 0.36 mmol), and HOAt (49 mg, 0.36 mmol) were dissolved in 2 mL of DMF. NMM (0.18 mL, 1.65 mmol) was added, followed by EDC (69 mg, 0.36 mmol). After stirring overnight at room temperature, the reaction mixture was purified by RP-HPLC to provide ((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide (90 mg, 55%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07893056B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-e4acb731eb85483682ff3d4b81845221 |
| Source note | uspto-grants-2011_02 |