4-[4-(2-Dimethylaminoethoxy)phenyl]butylamine → tert-butyl N-[N-(3,5-diamino-6-chloropyrazine-2-carbonyl)-N-[4-[4-[2-(dimethylamino)ethoxy]phenyl]butyl]carbamimidoyl]carbamate

HRID 1795842Notes

Reaction equation

HRID 1795842 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]N)=[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:48](CC)CC)C>>[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])[CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:17])[CH3:1])=[CH:11][CH:10]=1)=[NH:48])=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 221799624-[4-(2-Dimethylaminoethoxy)phenyl]butylamineHCID 68616177Triethylamine tetrahydrofuranHCID 178503948HCID 178503948, compound

Product 1

HCID 149251357tert-butyl N-[N-(3,5-diamino-6-chloropyrazine-2-carbonyl)-N-[4-[4-[2-(dimethylamino)ethoxy]phenyl]butyl]carbamimidoyl]carbamateYield 60%

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-62d168b450e14975a75212ea2ef6d43b
Source dataset
uspto-grants-2006_04
Patent number
US07030117B2

Reaction notes

Loading…