Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 86695127 | HCID 86695127 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 86695129 | HCID 86695129 | 96.7% |
Reaction Steps
To a solution of 3-[[(tert-butyldimethylsilyl)oxy]methyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraene (350 mg, 0.69 mmol, 1.00 equiv) in methanol (30 mL) was added hydrochloric acid (3 M in water, 1 mL) was added at 0° C. and the resulting solution was stirred for 1 h at room temperature. The reaction was quenched with NaHCO3/brine and extracted with EtOAc ((3×80 mL). The organic layers were combined and dried over anhydrous sodium sulfate. After filtration and concentration in vacuo, the residue was purified by a silica gel column with DCM/MeOH (30:1-10:1) to provide 260 mg (96%) of (12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl)methanol as a light yellow semi-solid. MS (ES): m/z 390 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09212190B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-e4a62379617e49248819a7e1d1be1458 |
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| Source note | uspto-grants-2015_12 |
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