Trifluoroacetic acid → 9-(azetidin-3-ylamino)-1-methyl-8-(1,1,1-trifluoropropan-2-yl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one trifluoroacetic acid

HRID 519088Notes

Reaction equation

HRID 519088 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[CH:27]([CH3:32])[C:28]([F:31])([F:30])[F:29])[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:34])[C:18](=[O:33])[NH:19][N:20]=2)[CH2:9]1)=O)(C)(C)C.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[NH:8]1[CH2:9][CH:10]([NH:12][C:13]2[C:26]([CH:27]([CH3:32])[C:28]([F:31])([F:29])[F:30])=[CH:25][C:24]3[O:23][CH2:22][C:21]4=[N:20][NH:19][C:18](=[O:33])[CH:17]([CH3:34])[N:16]4[C:15]=3[CH:14]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867274583-[4-Methyl-3-oxo-7-(2,2,2-trifluoro-1-methyl-ethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 867274599-(azetidin-3-ylamino)-1-methyl-8-(1,1,1-trifluoropropan-2-yl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one trifluoroacetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[4-methyl-3-oxo-7-(2,2,2-trifluoro-1-methyl-ethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-azetidine-1-carboxylic acid tert-butyl ester (0.020 g, 0.041 mmol) in DCM (3 mL) was added in TFA (0.5 mL) and the solution was stirred for 2 h. The solvent was removed in vacuo to give 9-(azetidin-3-ylamino)-1-methyl-8-(1,1,1-trifluoropropan-2-yl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one trifluoroacetic acid (0.015 g, 95%). LC/MS (Table 1, Method 5) Rt=2.166 min; MS m/z: 384 [M+H]+

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5c9b20c335d64f1db1107ea58c334e6b
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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