Dimethylamine → Trifluoroacetic acid

HRID 1521588Notes

Reaction equation

HRID 1521588 reaction equation
[CH3:1][C:2]([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]2[C:23]([CH3:26])=[N:24][N:25]=[C:18]2[CH2:17][CH2:16]3)[CH:12]=1)([CH3:6])[C:3]([OH:5])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:38]2[N:39]=[CH:40]C=CC=2N=N1.CNC.O1CCCC1.C(N(C(C)C)CC)(C)C.[F:68][C:69]([F:74])([F:73])[C:70]([OH:72])=[O:71]>CN(C)C=O>[F:68][C:69]([F:74])([F:73])[C:70]([OH:72])=[O:71].[CH3:38][N:39]([CH3:40])[C:3](=[O:5])[C:2]([CH3:6])([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]2[C:23]([CH3:26])=[N:24][N:25]=[C:18]2[CH2:17][CH2:16]3)[CH:12]=1)[CH3:1]

Participants

9

Reactant 6

HCID 674DimethylamineHCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89961700HCID 89961700, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 89962028HCID 89962028, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask containing the title compound from Example 54 Step A (10 mg, 0.03 mmol) and O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (13 mg, 0.034 mmol) in N,N-dimethylformamide (290 μL) was added a solution of dimethylamine in tetrahydrofuran (2 M, 17 μL, 0.034 mmol) followed by diisopropylethylamine (25 μL, 0.14 mmol). The reaction was stirred at room temperature overnight. The reaction was then acidified with trifluoroacetic acid, passed through a syringe filter and purified by HPLC (C18 column, 10 to 100% acetonitrile/water, both 0.1% v/v trifluoroacetic acid) to afford the title compound: LCMS m/z 376.06 [M+H]+; 1H NMR (500 MHz, CDCl3) 8.76 (s, 1H), 8.57 (s, 1H), 7.69 (s, 1H), 7.61-7.57 (m, 3H), 3.20-3.17 (m, 2H), 3.12-3.09 (m, 2H), 2.97 (br s, 3H), 2.81 (s, 3H), 2.59 (br s, 3H), 1.65 (s, 6H).

Workup

  1. custompassed through a syringe
  2. filtrationfilter
  3. custompurified by HPLC (C18 column, 10 to 100% acetonitrile/water

Sources & evidence

ORD record
ord-5e07e7d298fa4e129305cd090dc3420a
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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