Trifluoroacetic acid methylene chloride → HCID 178508350, compound

HRID 646737Notes

Reaction equation

HRID 646737 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:10]2[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=2)[C:13]([NH:15][C@@H:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[O:14])=[N:6][C:7]=1[C:8]#[N:9].C(Cl)Cl.[C:31](O)([C:33](F)(F)F)=O>CN1C(=O)CCC1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:10]2[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=2)[C:13]([NH:15][C@@H:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[O:14])=[N:6][C:7]=1[C:8]1[NH:3][C:2]([C@H:31]2[CH2:33][CH2:4][CH2:5][NH:6][CH2:7]2)=[N:1][N:9]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68650549HCID 68650549, compound

Product 1

HCID 178508350HCID 178508350, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-(5-amino-6-cyanopyrazine-2-yl)-N-[(1S)-2,3-dihydro-1H-inden-1-yl]benzamide (2.4 g, 6.6 mmol) and 1,1-dimethyl (3S)-3-(hydrazinocarbonyl)piperidine-1-carboxylate (2.4 g, 10.1 mmol) in NMP (3 mL) was heated to 180-200° C. for 1 h. The solvent was removed under reduced pressure. The residue obtained was stirred with CH2Cl2/TFA (20% v/v)) for 30 min., concentrated and purified by hplc. The compound was converted to the hydrochloride salt using a 4 M solution of HCl in dioxane to afford 3-(5-amino-6-{5-[(3S)-piperidin-3-yl]-4H-1,2,4-triazol-3-yl}pyrazin-2-yl)-N-[(1S)-2,3-dihydro-1H-inden-1-yl]benzamide: 1H NMR (400 MHz; CD3OD): 8.65 (s, 1H); 8.6 (d, 1H); 7.6 (t, 1H); 7.7-7.8 (m, 4H); 5.7 (t, 1H); 3.75-3.4 (m, 4H); 3.8-3.36 (m, 3H); 3.35-2.8 (m, 3H); 2.6 (m, 1H); 2.4 (m, 2H); 2.1-2.0(m, 4H); 1.3 (t, 3H); MS (EI) for C27H28N8O: 481 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue obtained
  3. concentrationconcentrated
  4. custompurified by hplc

Sources & evidence

ORD record
ord-8335e896675043fd9c3332f95c5b190e
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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