Trifluoroacetic acid → HCID 86727402, compound

HRID 519038Notes

Reaction equation

HRID 519038 reaction equation
C(OC([N:8]1[CH2:11][C:10]([O:13][C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[CH3:28])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:30])[C:19](=[O:29])[NH:20][N:21]=2)([CH3:12])[CH2:9]1)=O)(C)(C)C.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32]>C(Cl)Cl>[F:34][C:33]([F:36])([F:35])[C:31]([OH:37])=[O:32].[CH3:30][CH:18]1[N:17]2[C:22]([CH2:23][O:24][C:25]3[C:16]2=[CH:15][C:14]([O:13][C:10]2([CH3:12])[CH2:9][NH:8][CH2:11]2)=[C:27]([CH3:28])[CH:26]=3)=[N:21][NH:20][C:19]1=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727401HCID 86727401, compound

Product 1

HCID 86727402HCID 86727402, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4,7-dimethyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.024 g, 0.058 mmol) in DCM (2 mL) was added TFA (0.35 mL) and the mixture was stirred at ambient temperature for 2 h. The solvent was removed in vacuo. The residue was purified by preparative HPLC (Table 3, Method 6) to give 4,7-dimethyl-6-(3-methyl-azetidin-3-yloxy)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid as a pale solid (0.008 g, 44%). LC/MS (Table 1, Method 5) Rt=1.913 min.; MS m/z: 317 [M+H]+

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified by preparative HPLC (Table 3, Method 6)

Sources & evidence

ORD record
ord-bcac518f6a754fe6a3336b789bacfa56
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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