Ammonia → HCID 69620934, compound

HRID 1628310Notes

Reaction equation

C(OC([C@@H:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:9]([N:11]1[C:19]2[CH:18]=[C:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH:16]=[C:15]([C:26](O)=[O:27])[C:14]=2[CH2:13][CH2:12]1)=[O:10])=O)(C)(C)C.C[N:37]([C:39]([O:43]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:60]CN(C(C)C)C(C)C.[NH3:69].[CH3:70][CH:71]([OH:73])[CH3:72]>CN(C=O)C>[C:26]([C:15]1[CH:16]=[C:17]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH:18]=[C:19]2[C:14]=1[CH2:13][CH2:12][N:11]2[C:9](=[O:10])[C@@H:8]([NH:37][C:39](=[O:43])[O:73][C:71]([CH3:60])([CH3:72])[CH3:70])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)(=[O:27])[NH2:69]

Participants

Conditions

Temperature: 22 °C

Procedure

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).

Workup

customreaction
customwas partitioned between 600 ml of EtAc and 200 ml of water
customThe solvent was removed
customthe crude purified on a silica gel column (eluting with 10% MeOH in DCM)

Sources & evidence

ORD record: ord-d344d77c569f4f6991312e4a114c916f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785468B2

Reaction notes

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