Benzylamine → HCID 19040752, compound

HRID 1683922Notes

Reaction equation

HRID 1683922 reaction equation
[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15]3[N:16]=[C:17]([S:26][CH3:27])[N:18]=[N:19][C:20]=3[C:21](OCC)=[O:22])[CH:12]=2)[NH:7][CH:6]=1.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[CH3:28][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15]3[N:16]=[C:17]([S:26][CH3:27])[N:18]=[N:19][C:20]=3[C:21]([NH:36][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:22])[CH:12]=2)[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 19040757HCID 19040757, compound

Product 1

HCID 19040752HCID 19040752, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3-(2-dimethylaminoethyl)-5-(6-ethoxycarbonyl-3-methylthio-1,2,4-triazin-5-ylamino)-1H-indole (0.25 g, 0.62 mmol) in methylene chloride (5 mL) at room temperature under nitrogen was added dropwise benzylamine (0.14 mL, 1.25 mmol, 2.0 eq). The resulting reaction mixture was stirred at room temperature under nitrogen for 48 hours, and then filtered. The resulting yellow solid was recrystallized from methanol: ethyl acetate (4:1) to afford the title compound (0.063 g, 22%) as a yellow solid: mp, 207.0°-209.0° C.; FAB HRMS calculated for [C24H27N7OS.H+ ]482.2079, found 462.2054. Anal. calcd. for C24H27N7OS.3/4 H2O: C, 60.67; H, 6.05; N, 20.63. Found: C, 60.58; H, 5.73; N, 20.58.

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered
  3. customThe resulting yellow solid was recrystallized from methanol: ethyl acetate (4:1)

Sources & evidence

ORD record
ord-332967b244a7480882ba92a3e705af5a
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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