HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Methyl 4-(1-(indoline-7-carboxamido)cyclopropyl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | N-Boc-indoline-7-carboxylic acid | HCID 14977845 | — |
| Reactant | Methyl 4-(1-aminocyclopropyl)benzoate | HCID 45140209 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Methyl 4-(1-(indoline-7-carboxamido)cyclopropyl)benzoate | HCID 58017568 | — |
Reaction Steps
1-(tert-butoxycarbonyl)indoline-7-carboxylic acid (300 mg, 1.14 mmol), HATU (475 mg, 21.2 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (262 mg, 1.37 mmol) were added to acetonitrile (7.6 ml). The solution was cooled in an ice bath and DIPEA (695 ul, 3.99 mmol) was added. After 2 hr at RT, the mixture was poured into a solution of NaHCO3 (½ sat.) and washed 3 times with EtOAc. The combined organic layers were washed with brine and dried with Na2SO4. The solvent was removed and the crude mixture purified by flash chromatography on silica gel. The Boc group was removed with 1:1 TFA/DCM using the standard procedure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08158671B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-6ccbfe3566654562ad5557ca8317821b |
| Source note | uspto-grants-2012_04 |