Hydrochloric Acid → HCID 86727582, compound

HRID 519174Notes

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 86727580(3S,4S)-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 86727582HCID 86727582, compoundYield 53%

Conditions

Temperature: 20 °C

Procedure

A mixture of (3S,4S)-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 (0.035 g, 0.069 mmol) in HCl (4 M in EtOAc, 10 mL) was stirred at 20° C. for 2 h. The reaction mixture was concentrated in vacuo to give (R)-7-(2-fluoro-phenyl)-4-methyl-6-((3S,4S)-3-methyl-piperidin-4-yl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloride acid as a colorless solid (0.015 g, 53%). 1H NMR (400 MHz, MeOD) δ 7.52-7.41 (m, 1H), 7.35-7.18 (m, 3H), 6.93 (s, 1H), 6.86 (s, 1H), 4.90 (m, 1H), 4.65 (s, 2H), 3.47 (m, 1H), 3.22-2.94 (m, 4H), 2.84 (d, J=9.8 Hz, 1H), 2.55-2.27 (m, 2H), 2.00-1.80 (m, 3H), 1.51 (d, J=6.4 Hz, 3H), 1.00-0.80 (m, 3H). SFC (Table 1, Method 43), Rt=3.789 min., LC/MS (Table 1, Method 4) Rt=1.748 min.; MS m/z: 409 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-1f27b9ebfd414b31a07c536dd897ab3d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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