Hydrochloric Acid → (R)-8-ethyl-1-methyl-10-(3-methyl-azetidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one hydrochloride

HRID 519145Notes

Reaction equation

C(OC([N:8]1[CH2:11][C:10]([N:13]2[C:29]3[C:16](=[CH:17][C:18]4[O:19][CH2:20][C:21]5[N:26]([C:27]=4[CH:28]=3)[C@H:25]([CH3:30])[C:24](=[O:31])[NH:23][N:22]=5)[C:15]([CH2:32][CH3:33])=[CH:14]2)([CH3:12])[CH2:9]1)=O)(C)(C)C.[ClH:34]>>[ClH:34].[CH2:32]([C:15]1[C:16]2=[CH:17][C:18]3[O:19][CH2:20][C:21]4[N:26]([C:27]=3[CH:28]=[C:29]2[N:13]([C:10]2([CH3:12])[CH2:9][NH:8][CH2:11]2)[CH:14]=1)[C@H:25]([CH3:30])[C:24](=[O:31])[NH:23][N:22]=4)[CH3:33]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 867275363-((R)-8-ethyl-1-methyl-2-oxo-1,2,3,5-tetrahydro-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-10-yl)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86727537(R)-8-ethyl-1-methyl-10-(3-methyl-azetidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one hydrochlorideYield 39%

Procedure

A solution of 3-((R)-8-ethyl-1-methyl-2-oxo-1,2,3,5-tetrahydro-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-10-yl)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.04 g, 0.088 mmol) in HCl (4M in EtOAc, 3 mL) was stirred at −5-0° C. for 2 h. The solvent was removed in vacuo to give (R)-8-ethyl-1-methyl-10-(3-methyl-azetidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one hydrochloride (0.0122 g, 39%) as a yellow solid. 1H NMR (400 MHz, methanol-d4): δ 7.22 (s, 1H), 7.06 (s, 1H), 6.78 (s, 1H), 4.95 (m, 1H), 4.75 (m, 2H), 4.63-4.50 (m, 4H), 2.72 (q, J=7.6 Hz, 2H), 1.85 (s, 3H), 1.46 (d, J=6.8 Hz, 3H), 1.33 (t, J=7.6 Hz, 3H). LC/MS (Table 1, Method 4) Rt=1.591 min.; MS m/z: 354 [M+H]+.

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-2f98f0c24c704767b49332275fc75d35
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

Loading…