Hydrochloric Acid → (R)-7-bromo-4-methyl-6-((3R,4R)-3-methyl-piperidin-4-yl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloride

HRID 519186Notes

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[Br:28])[O:24][CH2:23][C:22]2[N:17]3[C@H:18]([CH3:30])[C:19](=[O:29])[NH:20][N:21]=2)[C@@H:10]([CH3:31])[CH2:9]1)=O)(C)(C)C.[ClH:32]>>[ClH:32].[Br:28][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:29])[C@H:18]3[CH3:30])=[CH:15][C:14]=1[C@@H:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]1[CH3:31]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 86727574(3R,4R)-4-((R)-7-bromo-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 86727598(R)-7-bromo-4-methyl-6-((3R,4R)-3-methyl-piperidin-4-yl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochlorideYield 82%

Procedure

A solution of (3R,4R)-4-((R)-7-bromo-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 (Example #199, Step D, 3 g, 6.08 mmol) in HCl (4M in EtOAc, 10 mL) was stirred at ambient temperature for 1 h. The organic solvent was removed in vacuo to give crude (R)-7-bromo-4-methyl-6-((3R,4R)-3-methyl-piperidin-4-yl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloride (2.2 g, 82%) as a white solid, which was used directly in the next step. LC/MS (Table 1, Method 25) Rt=0.720 min.; MS m/z: 393 [M+H]+& 395 [M+H+2]+.

Workup

customThe organic solvent was removed in vacuo

Sources & evidence

ORD record: ord-5a1a28ede0ce4d18b62a7ed20e46bbc1
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

Loading…