Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Glycolic Acid | HCID 757 | — |
| Reactant | Carbonate Ion | HCID 19660 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Isocyanate | HCID 105034 | — |
| Reactant | Carbodiimide | HCID 160435 | — |
| Reactant | HCID 89612991 | HCID 89612991 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 89613091 | HCID 89613091 | 59% |
Reaction Steps
To a solution of rel-(1R,3R)-3-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclopentanamine (10.8 mg), glycolic acid (1.9 mg), and 1-hydroxybenzotriazole (3.4 mg) in N,N-dimethylformamide (1.0 mL) was added a PS-Carbodiimide (Biotage Inc.) (100 mg), followed by stirring at room temperature overnight. To the reaction solution were added a PS-Isocyanate (Biotage Inc.) (50 mg) and a MP-Carbonate (Biotage Inc.) (50 mg), followed by stirring for four hours, and the insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure to obtain rel-N-[(1R,3R)-3-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclopentyl]-2-hydroxyacetamide (7.2 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08912180B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-49165c883a904880b0250806b60e992b |
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| Source note | uspto-grants-2014_12 |
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