HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-{2,6-Dichloro-3-[(2-fluoro-2-methyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 2-Fluoro-2-methylpropanoic acid | HCID 2782828 | — |
| Reactant | 2-{2,6-Dichloro-3-[aminomethyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid | HCID 67957315 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-{2,6-Dichloro-3-[(2-fluoro-2-methyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid | HCID 86666493 | — |
Reaction Steps
A mixture of 2-fluoroisobutyric acid (191 mg, 1.80 mmol), TBTU (578 mg, 1.80 mmol), DIPEA (1.00 mL, 5.7 mmol) and 10 mL DMF is stirred for 10 min and then the mixture is added to 2-{2,6-dichloro-3-[aminomethyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid (929 mg, 1.80 mmol) in 10 mL DMF and it is stirred overnight. Then the mixture is concentrated and purified via prep HPLC.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08674113B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-f3bad27079534488879a782be23cc20a |
| Source note | uspto-grants-2014_03 |