Oxalic Acid → HCID 178494165, compound

HRID 2177663Notes

Reaction equation

HRID 2177663 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:10]=[C:11]([NH:14][C:15]3[CH:20]=[N:19][CH:18]=[C:17]([O:21][C@@H:22]4[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]4)[N:16]=3)[NH:12][N:13]=2)=[CH:7][CH:6]=[C:5]([CH3:28])[N:4]=1.[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31]>ClCCl.CO>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:10]=[C:11]([NH:14][C:15]3[CH:20]=[N:19][CH:18]=[C:17]([O:21][C@@H:22]4[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]4)[N:16]=3)[NH:12][N:13]=2)=[CH:7][CH:6]=[C:5]([CH3:28])[N:4]=1.[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:10]=[C:11]([NH:14][C:15]3[CH:20]=[N:19][CH:18]=[C:17]([O:21][C@@H:22]4[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]4)[N:16]=3)[NH:12][N:13]=2)=[CH:7][CH:6]=[C:5]([CH3:28])[N:4]=1

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 178494163HCID 178494163, compound

Product 1

HCID 178494165HCID 178494165, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-[5-(2-methoxy-6-methyl-pyridin-3-yl)-2H-pyrazol-3-yl]-[6-(piperidin-3-yloxy)-pyrazin-2-yl]-amine (0.100 g, 0.26 mmol) in dichloromethane (10 mL) is added oxalic acid (0.012 mg, 0.13 mmol) dissolved in MeOH (0.1 mL) at 0° C. The reaction mixture is stirred for 60 min at room temperature and then the solvent evaporated to obtain a residue. The residue is triturated with diethyl ether (20 mL) followed by n-pentane (20 mL). The material is dried under high vacuum for 4 h to obtain the titled compound. Yield=0.095 g (77%). 1H NMR (400 MHz, DMSO-d6) δ 9.77 (s, 1H), 8.07 (s, 1), 7.95 (d, J=7.6 Hz, 1H), 7.55 (s, 1H), 6.95 (d, J=7.6 Hz, 1H), 6.79 (s, 1H), 5.33-5.24 (m, 1H), 3.97 (s, 3H), 3.45-3.30 (m, 2H), 3.18-3.09 (m, 1H), 3.08-2.98 (m, 1H), 2.42 (s, 3H), 2.05-1.85 (m, 2H), 1.74-1.63 (m, 1-1.18-1.10 (m, 1H); ES/MS m/z 382.4 [M+H]+.

Workup

  1. customthe solvent evaporated
  2. customto obtain a residue
  3. customThe residue is triturated with diethyl ether (20 mL)
  4. customThe material is dried under high vacuum for 4 h

Sources & evidence

ORD record
ord-ebf13970014e40df8a12276d507de490
Source dataset
uspto-grants-2015_06
Patent number
US09067920B2

Reaction notes

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