Trifluoroacetic acid → HCID 86727399, compound

HRID 519036Notes

Reaction equation

HRID 519036 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[CH:28]([CH3:30])[CH3:29])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:32])[C:19](=[O:31])[NH:20][N:21]=2)([CH3:12])[CH2:9]1)=O)(C)(C)C.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[CH:28]([C:27]1[CH:26]=[C:25]2[C:16]([N:17]3[C:22]([CH2:23][O:24]2)=[N:21][NH:20][C:19](=[O:31])[CH:18]3[CH3:32])=[CH:15][C:14]=1[O:13][C:10]1([CH3:12])[CH2:9][NH:8][CH2:11]1)([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727398HCID 86727398, compound

Product 1

HCID 86727399HCID 86727399, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(7-isopropyl-4-methyl-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 (0.049 g, 0.110 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 7) to give 7-isopropyl-4-methyl-6-(3-methyl-azetidin-3-yloxy)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid as a pale solid (0.042 g, 82%). LC/MS (Table 1, Method 5) Rt=2.233 min.; MS m/z: 345 [M+H]+

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified by preparative HPLC (Table 3, Method 7)

Sources & evidence

ORD record
ord-f1ed11b1839141adadfe7512d9594725
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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