Dimethylformamide → Trifluoroacetic acid

HRID 733072Notes

Reaction equation

HRID 733072 reaction equation
[S:1]1[C:12]2[C:4](=[CH:5][N:6]=[C:7]3[C:11]=2[CH:10]=[CH:9][NH:8]3)[CH:3]=[C:2]1[C:13]([OH:15])=O.CCN(C(C)C)C(C)C.CN(C([O:32]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:49][C:50]1[CH:51]=[C:52]([CH:66]=[CH:67][CH:68]=1)[C:53]([NH:55][C:56]1[CH:61]=[CH:60][CH:59]=[C:58]([C:62]([F:65])([F:64])[F:63])[CH:57]=1)=[O:54].CN([CH:72]=[O:73])C>>[F:63][C:62]([F:64])([F:65])[C:58]1[CH:57]=[C:56]([NH:55][C:53]([C:52]2[CH:51]=[C:50]([NH:49][C:13]([C:2]3[S:1][C:12]4[C:4]([CH:3]=3)=[CH:5][N:6]=[C:7]3[C:11]=4[CH:10]=[CH:9][NH:8]3)=[O:15])[CH:68]=[CH:67][CH:66]=2)=[O:54])[CH:61]=[CH:60][CH:59]=1.[C:72]([OH:73])([C:62]([F:65])([F:64])[F:63])=[O:32]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 23173713-amino-N-[3-(trifluoromethyl)phenyl]benzamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578391416H-Pyrrolo[2,3-b]thieno[2,3-d]pyridine-2-carboxylic acid

Product 2

HCID 6422Trifluoroacetic acidHCID 16041280HCID 16041280, compound

Procedure

6H-1-Thia-5,6-diaza-as-indacene-2-carboxylic acid (30 mg, 0.138 mmol) is mixed with DIEA (0.030 ml, 0.172 mmol) and HATU (57.71 mg, 0.151 mmol) in 2 ml DMF at room temperature. 3-Amino-N-(3-trifluoromethyl-phenyl)-benzamide (38.6 mg, 0.138 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 12.09 (s, 1H), 10.70, (s, 1H), 10.55 (s, 1H), 8.84 (s, 1H), 8.29 (s, 1H), 8.19 (s, 1H), 8.03-7.97 9 (m, 2H), 7.69 (d, 1H, J=7.6 Hz), 7.57-7.49 (m, 3H), 7.40 (d, 1H, J=7.6 Hz), 6.72 (dd, 1H, J=3.2, 1.6 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-42b087f50e7b4f319a66fd2a63500bd5
Source dataset
uspto-grants-2009_09
Patent number
US07589101B2

Reaction notes

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