Sodium Carbonate → HCID 86656632, compound

HRID 882891Notes

Reaction equation

HRID 882891 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([NH:18][C:19](=[O:41])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]([CH3:40])[CH2:26][CH2:27][NH:28][C:29]([C:31]2[C:36]([NH2:37])=[N:35][C:34]([NH2:38])=[C:33]([Cl:39])[N:32]=2)=[O:30])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH3:17].[Br:42][CH2:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[Br-:42].[Cl:8][C:9]1[CH:10]=[C:11]([NH:18][C:19](=[O:41])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][N+:25]([CH2:26][CH2:27][NH:28][C:29]([C:31]2[C:36]([NH2:37])=[N:35][C:34]([NH2:38])=[C:33]([Cl:39])[N:32]=2)=[O:30])([CH2:43][CH2:44][CH2:45][C:46]2[CH:47]=[CH:48][C:49]([O:52][CH3:53])=[CH:50][CH:51]=2)[CH3:40])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 127769961-(3-Bromopropyl)-4-methoxybenzeneHCID 86656633HCID 86656633, compound

Product 1

HCID 86656632HCID 86656632, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture comprising 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid [2-({4-[3-(3-chloro-4-ethoxy-phenyl)-ureido]-butyl}-methyl-amino)-ethyl]-amide trifluoroacetate (435 mg, 0.85 mmol), 1-(3-bromo-propyl)-4-methoxy-benzene (1.83 g, 7.99 mmol) and sodium carbonate (270 mg, 2.54 mmol) in acetone (8 mL) is heated at reflux for 11 days. After cooling to RT, the mixture is filtered and concentrated in vacuo. DCM is added and the precipitated solid is collected by filtration. The solid is crystallised from ethanol to afford the title compound. M+ 661. 1H NMR (400 MHz, DMSO-d6) δ 8.50 (1H, s), 8.29 (1H, t), 7.63 (2H, br), 7.62 (1H, d), 7.15 (1H, dd), 7.10 (2H, d), 6.99 (1H, d), 6.93 (2H, br), 6.81 (2H, d), 6.23 (1H, t), 4.01 (2H, q), 3.71 (3H, s), 3.61-3.56 (2H, m), 3.39-3.29 (4H, m), 3.08 (2H, q), 3.03 (3H, s), 2.49 (2H, t), 2.00-1.91 (2H, m), 1.72-1.64 (2H, m), 1.42 (2H, quint), 1.32 (3H, t).

Workup

  1. temperatureat reflux for 11 days
  2. filtrationthe mixture is filtered
  3. concentrationconcentrated in vacuo
  4. additionDCM is added
  5. filtrationthe precipitated solid is collected by filtration
  6. customThe solid is crystallised from ethanol

Sources & evidence

ORD record
ord-584e2c199ad84ba288747ea396ac486a
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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