Trifluoroacetic acid → 4-Methyl-6-(3-methyl-azetidin-3-ylamino)-7-trifluoromethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid

HRID 519033Notes

Reaction equation

HRID 519033 reaction equation
C(OC([N:8]1[CH2:11][C:10]([CH3:33])([NH:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[C:27]([F:30])([F:29])[F:28])[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:32])[C:18](=[O:31])[NH:19][N:20]=2)[CH2:9]1)=O)(C)(C)C.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>C(Cl)Cl>[F:37][C:36]([F:39])([F:38])[C:34]([OH:40])=[O:35].[CH3:32][CH:17]1[N:16]2[C:21]([CH2:22][O:23][C:24]3[C:15]2=[CH:14][C:13]([NH:12][C:10]2([CH3:33])[CH2:11][NH:8][CH2:9]2)=[C:26]([C:27]([F:29])([F:30])[F:28])[CH:25]=3)=[N:20][NH:19][C:18]1=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867273943-Methyl-3-(4-methyl-3-oxo-7-trifluoromethyl-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 867273954-Methyl-6-(3-methyl-azetidin-3-ylamino)-7-trifluoromethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acidYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methyl-3-(4-methyl-3-oxo-7-trifluoromethyl-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (0.010 g, 0.021 mmol) in DCM (1 mL) and TFA (0.25 mL) was stirred for 1 h at ambient temperature. The solvent was removed in vacuo and the residue was purified by preparative HPLC (Table 3, Method 10) to give 4-methyl-6-(3-methyl-azetidin-3-ylamino)-7-trifluoromethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid as a white solid (0.0045 g, 44%). LC/MS (Table 1, Method 4) Rt=1.441 min; MS m/z: 370 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by preparative HPLC (Table 3, Method 10)

Sources & evidence

ORD record
ord-f5de5e7a31f141b5bfdc60deda3eac14
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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