Trifluoroacetic acid → 6,6′-(2,2-Di-3-pyridinylethylidene)bis[2-pyridinamine]

HRID 2099577Notes

Reaction equation

HRID 2099577 reaction equation
C(OC([NH:8][C:9]1[N:14]=[C:13]([CH:15]([C:29]2[N:34]=[C:33]([NH:35]C(=O)OC(C)(C)C)[CH:32]=[CH:31][CH:30]=2)[CH:16](C2C=CC=CN=2)[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][CH:10]=1)=O)(C)(C)C.[C:43](O)([C:45](F)(F)F)=O>C(Cl)Cl>[NH2:35][C:33]1[N:34]=[C:29]([CH:15]([C:13]2[N:14]=[C:9]([NH2:8])[CH:10]=[CH:11][CH:12]=2)[CH:16]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[C:12]2[CH:13]=[N:14][CH:9]=[CH:43][CH:45]=2)[CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68798013HCID 68798013, compound

Product 1

HCID 116677886,6′-(2,2-Di-3-pyridinylethylidene)bis[2-pyridinamine]

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of tert-butyl 6-(1-{6-[(tert-butoxycarbonyl)amino]pyridin-2-yl}-2-pyridin-2-yl-2-pyridin-3-ylethyl)pyridin-2-ylcarbamate (0.12 g, 0.211 mmol) in CH2Cl2 (2 mL) was added CF3COOH (2 mL) and stirred for 1 h. The mixture was concentrated and the residue was dissolved in MeOH (3 mL). Potassium carbonate (200 mg) was added and stirred for 0.5 h. The mixture was filtered and the filtrate concentrated. The residue was purified by silica gel chromatography (10% MeOH in CH2Cl2) to give the title compound. 1H-NMR (500 MHz, DMSO-d6) δ 8.60 (s, 2H), 8.32 (d, 2H, J=4.6), 7.92 (d, 2H, J=7.8), 7.41 (s, 2H), 7.28(dd, 2H, J=7.7, 4.7), 7.15 (broad, 4H), 6.60 (d, 2H, J=7.4), 6.46 (s,2H), 5.25 (d, 1H, J=10.3), 4.98 (broad, 1H). LRMS m/z (M+H) Calcd: 369.4, found: 369.1.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in MeOH (3 mL)
  3. additionPotassium carbonate (200 mg) was added
  4. stirringstirred for 0.5 h
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated
  7. customThe residue was purified by silica gel chromatography (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9ee304183cc7478da59c6ce36bff028c
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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