Hydrochloric Acid → (R)-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 519137Notes

Reaction equation

HRID 519137 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)[CH:14]=[CH: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)[CH:13]=[CH:14][C:15]3=[CH:16][C:17]=1[O:18][CH2:19]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 867275273-methyl-3-((R)-1-methyl-2-oxo-1,2,3,5-tetrahydro-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-10-yl)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86727525(R)-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 85%

Procedure

To a solution of HCl (4M in EtOAc, 40 mL) was added 3-methyl-3-((R)-1-methyl-2-oxo-1,2,3,5-tetrahydro-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-10-yl)-azetidine-1-carboxylic acid tert-butyl ester (4 g, 9.4 mmol) at 0° C. and the reaction mixture was stirred for 30 min. The resulting precipitate was collected by filtration and recrystallized in EtOH to give (R)-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 (2.6 g, 85%). 1H NMR (CD3OD, 400 MHz): δ 7.27 (d, J=12.8 Hz, 2H), 6.84 (s, 1H), 6.50 (s, 1H), 5.04 (d, J=6.5 Hz, 1H), 4.79 (m, 2H), 4.62-4.55 (m, 4H), 1.89 (s, 3H), 1.47 (d, J=6.5 Hz, 3H). LC/MS (Table 1, Method 5) Rt=1.988 min; MS m/z: 326 [M+1]+. SFC (Table 1, Method 37) Rt=2.169 min.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customrecrystallized in EtOH

Sources & evidence

ORD record
ord-6ed5f789890146c3b5fa1066c488d00a
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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