Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-(Chloromethyl)benzoyl chloride | HCID 70136 | — |
| Reactant | tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate | HCID 57717474 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59737342 | HCID 59737342 | 63% |
Reaction Steps
To a suspension of amine 4 (0.45 g, 1.55 mmol) in DCM (6.84 mL), cooled to −20° C., was added triethylamine (0.65 mL, 4.65 mmol) followed by a solution of 4-(chloromethyl)benzoyl chloride 73 (0.322 g, 1.71 mmol) in DCM (2.28 mL) via canula. The cold bath was then removed and the reaction mixture was stirred at room temperature for 1 h, washed with saturated NH4Cl, saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. The crude material was recrystallized from 30% AcOEt in hexane to give title compound 74 (0.431 g, 63% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08598168B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-8b3596d8753f4b91ae1ae2d9e7dc9eb8 |
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| Source note | uspto-grants-2013_12 |
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