Hydrochloric Acid → 6-(Azetidin-3-ylamino)-7-fluoro-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloric acid

HRID 518978Notes

Reaction equation

HRID 518978 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[F:27])[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:29])[C:18](=[O:28])[NH:19][N:20]=2)[CH2:9]1)=O)(C)(C)C.[ClH:30]>CCOC(C)=O>[ClH:30].[NH:8]1[CH2:9][CH:10]([NH:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[F:27])[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:29])[C:18](=[O:28])[NH:19][N:20]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867273273-(7-Fluoro-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 867273286-(Azetidin-3-ylamino)-7-fluoro-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloric acidYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 3-(7-fluoro-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (0.110 g, 0.271 mmol) in EtOAc (10 mL) was added an EtOAc solution saturated with hydrogen chloride (3 mL). The reaction mixture was stirred at rt for 3 h then concentrated in vacuo and the residue was purified by preparative HPLC (Table 3, Method 1)) to give 6-(azetidin-3-ylamino)-7-fluoro-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloric acid as a white solid (0.026 g, 31%). LC/MS (Table 1, Method 5) Rt=1.853 min.; MS m/z: 306 [M+H]+.

Workup

  1. concentrationthen concentrated in vacuo
  2. customthe residue was purified by preparative HPLC (Table 3, Method 1))

Sources & evidence

ORD record
ord-32d2c5b49090403ba8fe969ddca77bbf
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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