4-[4-(2-Dimethylaminoethoxy)phenyl]butylamine → N-tert-Butyloxycarbonyl-N'-(3,5-diamino-6-chloropyrazine-2-carbonyl)-N''-{4-[4-(2-dimethylaminoethoxy)phenyl]butyl}guanidine

HRID 254355Notes

Reaction equation

HRID 254355 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:8][CH:7]=1.[C:18]([O:22][C:23]([NH:25][C:26](=[N:29][C:30]([C:32]1[C:37]([NH2:38])=[N:36][C:35]([NH2:39])=[C:34]([Cl:40])[N:33]=1)=[O:31])SC)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C1COCC1.C(N(CC)CC)C>[C:18]([O:22][C:23]([NH:25][C:26]([NH:29][C:30]([C:32]1[C:37]([NH2:38])=[N:36][C:35]([NH2:39])=[C:34]([Cl:40])[N:33]=1)=[O:31])=[N:16][CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:17])=[CH:7][CH:8]=1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 221799624-[4-(2-Dimethylaminoethoxy)phenyl]butylamineHCID 178503948HCID 178503948, compound

Product 1

HCID 22185172N-tert-Butyloxycarbonyl-N'-(3,5-diamino-6-chloropyrazine-2-carbonyl)-N''-{4-[4-(2-dimethylaminoethoxy)phenyl]butyl}guanidineYield 60%

Reagents, catalysts & solvents 1

HCID 68616177Triethylamine tetrahydrofuranSolvent

Procedure

A suspension of compound 63 (0.22 g, 0.93 mmol) and 64 (0.33 g, 0.92 mmol) in THF/triethylamine (11 mL, 10/1) was stirred at room temperature for 48 h. After this time, a clear solution was formed. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, 10:1:0.1 chloroform/methanol/concentrated ammonium hydroxide) to provide the guanidine 65 (0.3 g, 60%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.42 (s, 9H), 1.55 (m, 4H), 2.19 (s, 6H), 2.58 (m, 4H), 3.99 (m, 2H), 6.83 (d, 2H), 7.12 (d, 2H), 7.40 (br s, 2H), 9.02 (m, 2H).

Workup

  1. customAfter this time, a clear solution was formed
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography (silica gel, 10:1:0.1 chloroform/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-87f22aa070a34c2eabbeaa857fe1557c
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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