Hydrochloric Acid → HCID 86727612, compound

HRID 519195Notes

Reaction equation

C(OC([N:8]1[CH2:13][C@@H:12]([CH3:14])[N:11]([C:15]2[CH:16]=[C:17]3[C:26](=[CH:27][C:28]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[F:35])[O:25][CH2:24][C:23]2[N:18]3[C@H:19]([CH3:37])[C:20](=[O:36])[NH:21][N:22]=2)[CH2:10][C@@H:9]1[CH3:38])=O)(C)(C)C.[ClH:39]>>[ClH:39].[CH3:14][C@@H:12]1[CH2:13][NH:8][C@@H:9]([CH3:38])[CH2:10][N:11]1[C:15]1[CH:16]=[C:17]2[C:26](=[CH:27][C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35])[O:25][CH2:24][C:23]1[N:18]2[C@H:19]([CH3:37])[C:20](=[O:36])[NH:21][N:22]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 86727614HCID 86727614, compound

Product 1

HCID 86727612HCID 86727612, compoundYield 99%

Procedure

A solution of (2S,5R)-4-[(R)-7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (isomer 2, SFC (Table 1, Method 55), Rt=5.643 min., 0.05 g, 0.095 mmol) in HCl (4 M in EtOAc, 2 mL) was stirred at ambient temperature for 1 h. The solvent was concentrated in vacuo to give (R)-6-((2R,5S)-2,5-dimethyl-piperazin-1-yl)-7-(2-fluoro-phenyl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloride (0.040 g, 99%) as a white solid. 1H NMR (CD3OD, 400 MHz) δ 7.27-7.40 (m, 1H), 7.22-7.26 (m, 2H), 7.15-7.22 (m, 1H), 7.05 (s, 1H), 6.96 (s, 1H), 4.90-4.91 (m, 1H), 4.59-4.70 (m, 2H), 3.09-3.25 (m, 3H), 3.03 (m, 1H), 2.78-2.87 (m, 1H), 2.49 (m, 1H), 1.49 (d, J=6.5 Hz, 3H), 1.24 (d, J=6.5 Hz, 3H), 0.76 (d, J=6.3 Hz, 3H). LC/MS (Table 1, Method 4) Rt=1.739 min.; MS m/z: 424 [M+H]+. SFC (Table 1, Method 55), Rt=6.795 min.

Workup

concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record: ord-87bf20526fbb42809ed9646e2e930a3f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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