Hydrochloric Acid → HCID 86727590, compound

HRID 519180Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[O:24][CH2:23][C:22]2[N:17]3[C@H:18]([CH3:36])[C:19](=[O:35])[NH:20][N:21]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:37]>>[ClH:37].[F:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:27]1[CH:26]=[C:25]2[C:16]([N:17]3[C:22]([CH2:23][O:24]2)=[N:21][NH:20][C:19](=[O:35])[C@H:18]3[CH3:36])=[CH:15][C:14]=1[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 86727589HCID 86727589, compound

Product 1

HCID 86727590HCID 86727590, compoundYield 81%

Procedure

To HCl (1 M in EtOAc, 10 mL) was added 4-[(R)-7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-piperidine-1-carboxylic acid tert-butyl ester (1 g, 2.20 mmol) and the reaction mixture was stirred at ambient temperature for 1 h. The solvent was removed in vacuo to give (R)-7-(2-fluoro-phenyl)-4-methyl-6-piperidin-4-yl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloride (0.65 g, 81%) as a yellow solid. 1H NMR (400 MHz, methanol-d4) δ 7.51-7.41 (m, 1H), 7.32-7.27 (m, 2H), 7.23 (t, J=9.0 Hz, 1H), 7.03 (s, 1H), 6.87 (s, 1H), 5.01-4.95 (m, 1H), 4.70-4.60 (m, 2H), 3.50-3.38 (m, 2H), 3.01-2.69 (m, 3H), 2.05 (m, 2H), 1.90 (m, 2H), 1.52 (m, 3H). LCMS (Table 1, Method 5) Rt=2.351 min; MS m/z: 395[M+H]+.

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-09f73ba3d8f24dac9b5eab6de0284058
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

Loading…