Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(3-Chloropropyl)morpholine | HCID 95834 | — |
| Reactant | HCID 136016309 | HCID 136016309 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57642327 | HCID 57642327 | 44% |
Reaction Steps
A mixture of 0.322 g (0.00103 mole) of 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-hydroxy-2H-1,4-benzodiazepin-2-one (Iqq), 6 mL of dimethylformamide, 0.132 g (0.00124 mole) of sodium carbonate and 0.2028 g (0.00124 mole) of 4-(3-chloropropyl)-morpholine was stirred 50° C. under an atmosphere of argon for 24 hours. The mixture was then cooled and partitioned between ethyl acetate and water. The aqueous phase was reextracted with ethyl acetate and the ethyl acetate extracts were then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with acetonitrile-methanol (90:10), to provide 0.199 g of 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-(3-(4-morpholinyl)propoxy)-2H-1,4-benzodiazepin-2-one (Ik). MH+/Z=439.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07524840B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-6bd1ae83c0ab4bf9bc03923bca93090b |
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| Source note | uspto-grants-2009_04 |
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