Hydrochloric Acid → HCID 86727575, compound

HRID 519170Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][C@@H: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)[C@@H:10]([CH3:37])[CH2:9]1)=O)(C)(C)C.[ClH:38]>>[ClH:38].[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[C@@H:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]1[CH3:37]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 86727573(3R,4R)-4-[(R)-7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-3-methyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86727575HCID 86727575, compoundYield 98%

Conditions

Temperature: 20 °C

Procedure

A mixture of (3R,4R)-4-[(R)-7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (0.076 g, 0.149 mmol) in HCl (4M in EtOAc, 15 mL) was stirred at 20° C. for 1 h. The reaction mixture was concentrated in vacuo to give (R)-7-(2-fluoro-phenyl)-4-methyl-6-((3R,4R)-3-methyl-piperidin-4-yl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloride acid (0.065 g, 98%). 1H NMR (MeOD, 400 MHz) δ 7.50-7.41 (m, 1H), 7.32-7.19 (m, 3H), 6.91 (brs, 1H), 6.86 (s, 1H), 4.80 (m, 1H), 4.70-4.59 (m, 2H), 3.48 (m, 1H), 3.15-2.98 (m, 2H), 2.82 (m, 1H), 2.43 (m, 1H), 1.88 (m, 2H), 1.50 (d, J=6.4 Hz, 3H), 0.91 (brs, 3H). LC/MS (Table 1, Method 4) Rt=1.534 min.; MS m/z: 409 [M+H]+. SFC (Table 1, Method 43), Rt=1.341 min.

Workup

concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-1e494ee9d7a94eab94345b4b4d35a6a9
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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