Acetic Acid → HCID 178476659, compound

HRID 2177662Notes

Reaction equation

HRID 2177662 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:32])(=[O:31])[CH3:30]>ClCCl>[C:29]([OH:32])(=[O:31])[CH3:30].[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

4

Reactant 2

HCID 176Acetic AcidHCID 178494163HCID 178494163, compound

Product 1

HCID 178476659HCID 178476659, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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 acetic acid (0.015 mL, 0.26 mmol) dissolved in dichloromethane (1 mL) at 0° C. The reaction mixture is stirred for 60 min at room temperature and then the solvent is 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 desired product. Yield=0.060 g (51.8%). 1H NMR (400 MHz, DMSO-d6) δ 12.40 (bs, 1H), 9.70 (s, 1H), 8.02 (d, J=7.6 Hz, 1H), 7.98 (s, 1H), 7.46 (s, 1H), 6.94 (d, J=7.6 Hz, 1H), 6.90 (s, 1H), 4.97-4.38 (m, 1H), 3.98 (s, 3H), 3.20-3.13 (m, 1H), 2.83-2.74 (m, 1H), 2.66-2.56 (m, 1H), 2.42 (s, 3H), 2.14-2.03 (m, 1H), 1.89 (s, 3H), 1.74-1.62 (m, 1H), 1.61-1.51 (m, 1H), 1.50-1.40 (m, 1H), 1.30-1.20 (m, 1H); ES/MS m/z 382.5 [M+H]+.

Workup

  1. customthe solvent is 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-90baf960f3954664a244eb1378271845
Source dataset
uspto-grants-2015_06
Patent number
US09067920B2

Reaction notes

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