HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(3S)-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 66936103 | HCID 66936103 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(3S)-3,4-dimethyl-1-piperazinyl]-5-fluoro-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide | HCID 86636942 | 67.4% |
Reaction Steps
(2R)-3-Cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (0.184 g, 0.60 mmol), 4-[(3S)-3,4-dimethyl-1-piperazinyl]-5-fluoro-6-hydrazino-2-methylpyrimidine (0.161 g, 0.63 mmol), NMM (0.21 mL, 1.89 mmol), HOAt (0.086 g, 0.63 mmol), and EDC (0.121 g, 0.63 mmol) were dissolved in DMF (4 mL), and the reaction was stirred overnight. Purified by RP-HPLC to provide [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(3S)-3,4-dimethyl-1-piperazinyl]-5-fluoro-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.219 g, 64%). 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-c5809e44c6ee437181fdf4eae5618fd0 |
| Source note | uspto-grants-2011_02 |