Succinic Acid → HCID 178494164, compound

HRID 2177664Notes

Reaction equation

HRID 2177664 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:36])(=[O:35])[CH2:30][CH2:31][C:32]([OH:34])=[O:33]>ClCCl.C(O)C>[C:29]([OH:36])(=[O:35])[CH2:30][CH2:31][C:32]([OH:34])=[O:33].[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 1110Succinic AcidHCID 178494163HCID 178494163, compound

Product 1

HCID 178494164HCID 178494164, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 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 (0.1 g, 0.26 mmol) in dichloromethane (10 mL) is added succinic acid (0.015 g, 0.13 mmol) dissolved in ethanol (1 mL, dissolved at 50° C.) at room temperature. The reaction mixture is stirred for 2 h at room temperature. The solvent is evaporated and the residue obtained is triturated with diethyl ether (20 mL) followed by n-pentane (20 mL). The material is dried under high vacuum for 8 h to obtain the title compound. Yield=0.102 g (78%). 1H NMR (400 MHz, DMSO-d6) δ 12.4 (bs, 1H), 9.72 (s, 1H), 8.05-7.96 (m, 2H), 7.48 (s, 1H), 6.93 (d, J=7.6 Hz, 1H), 6.86 (s, 1H), 5.06-4.97 (m, 1H), 3.97 (s, 3H), 2.90-2.81 (m, 1H), 2.74-2.62 (m, 1H), 2.42 (s, 3H), 2.30 (s, 2H), 2.09-2.01 (m, 1H), 1.80-1.60 (m, 2H), 1.57-1.46 (m, 1H), 1.14-1.10 (m, 1H), 1.10-1.00 (m, 1H); ES/MS m/z 382.4 [M+H]+.

Workup

  1. customThe solvent is evaporated
  2. customthe residue obtained
  3. customis triturated with diethyl ether (20 mL)
  4. customThe material is dried under high vacuum for 8 h

Sources & evidence

ORD record
ord-ab08103ff96f4e9fae2d158c14119f6a
Source dataset
uspto-grants-2015_06
Patent number
US09067920B2

Reaction notes

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