HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropylamine → 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-(2-Amino-1,3-thiazol-4-yl)benzoic acid | HCID 613179 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide | HCID 59228792 | 95% |
Reaction Steps
4-(2-Amino-thiazol-4-yl)-benzoic acid (4.4 g, 20 mmol) was dissolved in DMF (100 mL) and treated with HATU (1.1 eq. 8.4 g) and DIEA (2.1 eq, 7.5 mL) and stirred for 15 minutes. Then cyclopropyl amine (1.1 eq, 1.5 mL) was added and the mixture stirred at ambient temperature for 1 hr. The reaction was diluted with 100 mL of water, extracted with EtOAc (3×100 mL) dried with brine (100 mL) and then Na2SO4 and the solvents removed. The resulting solid was triturated with ether to give the product >95% purity by HPLC. MS: 260.3 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07595398B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-2df0e55deaa9479ebeb51b0192092a6d |
| Source note | uspto-grants-2009_09 |