HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonyl chloride → methanesulfonic acid 2-{4-[N'-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-{4-[N'-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethanol | HCID 66841059 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | methanesulfonic acid 2-{4-[N'-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethyl ester | HCID 76837803 | 35% |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
Compound 93, 2-{4-[N′-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethanol (680 mg., 2 mmol) was dissolved in methylene chloride (10 mL) and to the reaction mixture was added diisopropylethylamine (0.6 mL, 3 mmol). The reaction was chilled to 0° C. To the reaction was added methanesulfonyl chloride (251 mg., 2.2 mmol). After fifteen minutes, the reaction was washed with saturated aqueous ammonium chloride (2×2 mL), dried with sodium sulfate, and purified by column chromatography to give Compound 95, methanesulfonic acid 2-{4-[N′-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethyl ester (290 mg., 0.7 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07872005B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-218dce0d809047ff952a21757582eda0 |
| Source note | uspto-grants-2011_01 |