Hydrochloric Acid → HCID 86727539, compound

HRID 519148Notes

Reaction equation

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

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 86727541HCID 86727541, compound

Product 1

HCID 86727539HCID 86727539, compoundYield 85%

Procedure

A mixture of 3-methyl-3-((R)-1-methyl-2-oxo-1,2,3,5,8,9-hexahydro-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-10-yl)-azetidine-1-carboxylic acid tert-butyl ester (enantiomer 2, 0.04 g, 0.094 mmol) in HCl (4M in EtOAc, 5 mL) was stirred at ambient temperature for 20 min. The solvent was removed in vacuo to give (R)-1-methyl-10-(3-methyl-azetidin-3-yl)-3,5,9,10-tetrahydro-8H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one hydrochloride (0.026 g, 0.079 mmol, 85%). 1H NMR (400 MHz, DMSO-d6): δ 10.68 (s, 1H), 6.78 (s, 1H), 5.80 (s, 1H), 4.98 (m, 1H), 4.45 (s, 2H), 4.11 (m, 4H), 3.30-3.20 (m, 2H), 2.74 (m, 2H), 1.39 (s, 3H), 1.20 (d, J=6.4 Hz, 3H). LC/MS (Table 1, Method 41) Rt=2.422 min; MS m/z: 328 [M+H]+. SFC (Table 1, Method 37) Rt=10.675 min.

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-005730bdcac74b7eb378b26d44e5d7c8
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

Loading…