Dimethylformamide → Trifluoroacetic acid

HRID 733074Notes

Reaction equation

HRID 733074 reaction equation
[CH3:1][N:2]1[C:13]2[C:5](=[CH:6][N:7]=[C:8]3[C:12]=2[CH:11]=[CH:10][NH:9]3)[CH:4]=[C:3]1[C:14]([OH:16])=O.CCN(C(C)C)C(C)C.CN(C([O:33]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:50][C:51]1[CH:52]=[C:53]([NH:57][C:58](=[O:69])[C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:67])[F:66])[CH:60]=2)[CH:54]=[CH:55][CH:56]=1.CN([CH:73]=[O:74])C>>[F:66][C:65]([F:67])([F:68])[C:61]1[CH:60]=[C:59]([CH:64]=[CH:63][CH:62]=1)[C:58]([NH:57][C:53]1[CH:52]=[C:51]([NH:50][C:14]([C:3]2[N:2]([CH3:1])[C:13]3[C:5]([CH:4]=2)=[CH:6][N:7]=[C:8]2[C:12]=3[CH:11]=[CH:10][NH:9]2)=[O:16])[CH:56]=[CH:55][CH:54]=1)=[O:69].[C:73]([OH:74])([C:65]([F:68])([F:67])[F:66])=[O:33]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 20117519N-(3-aminophenyl)-3-(trifluoromethyl)benzamideHCID 57839142HCID 57839142, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 15951513HCID 15951513, compound

Procedure

1-Methyl-1,6-dihydro-1,5,6-triaza-as-indacene-2-carboxylic acid (35 mg, 0.162 mmol) is mixed with DIEA (0.030 ml, 0.172 mmol) and HATU (67.8 mg, 0.178 mmol) in 2 ml DMF at room temperature. N-(3-Amino-phenyl)-3-trifluoromethylbenzamide (45.53 mg, 0.162 mmol) is added into the reaction mixture 0.5 hours later. After stirring at room temperature for 2 hours, the reaction mixture is concentrated and purified by Prep-HPLC to afford the title compound as a TFA salt: 1H NMR 400 MHz (DMSO-d6) δ 12.37 (s, 1H), 10.56, (s, 2H), 8.87 (s, 1H), 8.40 (s, 1H), 8.33 (s, 1H), 8.29 (d, 1H, J=8.0 Hz), 7.98 (d, 1H, J=7.6 Hz), 7.84 (t, 1H, J=8.0 Hz), 7.68 (s, 1H), 7.57-7.54 (m, 3H), 7.37 (t, 1H, J=8.0 Hz), 7.09-7.07 (m, 1H), 4.32 (s, 3H) Hz; MS m/z 481.1 (M+1).

Workup

  1. concentrationthe reaction mixture is concentrated
  2. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-deb1456e21fa485ab0872cd7bc79fdcd
Source dataset
uspto-grants-2009_09
Patent number
US07589101B2

Reaction notes

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