Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | HCID 67496520 | HCID 67496520 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69620934 | HCID 69620934 | 53% |
Reaction Steps
To a 100 ml flask was added (S)-1-(2-(tert-butoxycarbonyl)-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxylic acid 60.A (430 mg, 0.88 mmole), HBTU (669 mg, 1.8 mmole), 20 ml of DMF, DIEA (461 ul, 2.6 mmole) and 2.0 m ammonia solution in 2-propanol (3 ml, 5.3 mmole). The reaction was stirred at 22° C. for 2 hours, at which time the crude reaction was partitioned between 600 ml of EtAc and 200 ml of water. The solvent was removed and the crude purified on a silica gel column (eluting with 10% MeOH in DCM) to give (S)-tert-butyl 1-(4-carbamoyl-6-(pyridin-4-yl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate 60.B as a white solid (228 mg, 53% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08785468B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-d344d77c569f4f6991312e4a114c916f |
|---|
| Source note | uspto-grants-2014_07 |
|---|
