Ethanol → HCID 69596591, compound

HRID 1243314Notes

Reaction equation

HRID 1243314 reaction equation
CO[C:3]1[CH:19]=[CH:18][C:17](OCCCCC)=[CH:16][C:4]=1[CH2:5][C:6](=[CH:9]N1CCOCC1)[C:7]#[N:8].Cl.N[C:28]1C=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.[NH2:35][C:36]([NH2:38])=[NH:37].C[CH2:40][O-:41].[Na+].[Na+].[Cl-].CC[OH:47]>>[NH2:37][C:36]1[N:38]=[C:7]([NH2:8])[C:6]([CH:5]([O:47][CH2:32][CH2:31][CH2:30][CH:29]([O:41][CH3:40])[CH3:28])[C:4]2[CH:3]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][N:35]=1

Participants

7

Reactant 6

HCID 702Ethanol2×HCID 5234Sodium ChlorideHCID 5742Guanidine HydrochlorideHCID 8870Benzenamine hydrochloride (1:1)HCID 2723922Sodium ethoxideHCID 73099203HCID 73099203, compound

Product 1

HCID 69596591HCID 69596591, compound

Procedure

A solution of 10 (0.835 g, 2.43 mmol) and aniline hydrochloride (0.47 g, 3.64 mmol) in absolute EtOH (10 mL) was refluxed for 1 h. In a separate flask, guanidine hydrochloride (1.09 g, 11.4 mmol) was added to a solution of NaOEt prepared by dissolving clean metallic Na (345 mg, 15 mmol) in absolute EtOH (15 mL) and the flask was swirled manually for 5 min. The entire contents of the second flask (including the NaCl) were added to the first, and the combined mixture was refluxed for 18 h and then filtered while hot. TLC analysis of the filtrate (silica gel, 10:1 EtOAc-MeOH) showed the product (3a) as a major UV-absorbing spot (Rf0.3), along with several fast-moving impurities. Flash chromatography (silica gel, 18 g, 2×15 cm) with 10:1 EtOAc-MeOH as the eluent afforded an amorphous solid, which on recrystallization from aqueous EtOH afforded 3a as white flakes (540 mg, 70%); mp 140–141° C.; IR (KBr) ν 3410, 3330, 3230, 3120, 2990, 2950, 2910sh, 2870, 2830, 1665, 1635, 1605, 1565, 1540, 1505, 1480, 1460, 1440, 1420 cm−1; 1H NMR (200 MHz, DMSO-d6) δ 0.87 (m, 3H, pentyl Me), 1.33 (m, 4H, pentyl 3- and 4-CH2), 1.64 (p, J=7 Hz, 2H, pentyl 2-CH2), 3.47 (s, 2H, bridge CH2), 3.73 (s, 3H, OMe), 3.83 (t, J=7 Hz, 2H, OCH2), 5.65 (broad s, 2H, NH2), 6.02 (br s, 2H, NH2), 6.64 (d, J=3 Hz, 1H, aryl H-6), 6.70 (dd, J=8 Hz, J=3H, 1H, aryl H-4), 6.87 (d, J=8 Hz, 1H, aryl H-3), 7.39 (s, 1H, pyrimidine H-6).

Workup

  1. customprepared
  2. additionwere added to the first, and the combined mixture
  3. temperaturewas refluxed for 18 h
  4. filtrationfiltered while hot
  5. customFlash chromatography (silica gel, 18 g, 2×15 cm) with 10:1 EtOAc-MeOH as the eluent afforded an amorphous solid, which
  6. customon recrystallization from aqueous EtOH

Sources & evidence

ORD record
ord-7532eda8521b495093472fb9f602f83f
Source dataset
uspto-grants-2006_10
Patent number
US07119095B2

Reaction notes

Loading…