Methylamine → HCID 15222249, compound

HRID 129002Notes

Reaction equation

HRID 129002 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]3[C:12]([CH2:13][C:14]([OH:16])=O)=[C:11]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:10]=[C:7]3[N:8]([CH3:9])[C:4]=2[CH:3]=1.[CH3:25][NH2:26]>O1CCCC1>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]3[C:12]([CH2:13][C:14]([NH:26][CH3:25])=[O:16])=[C:11]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:10]=[C:7]3[N:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 15222258HCID 15222258, compound

Product 1

HCID 15222249HCID 15222249, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 1.7 g (0.005 mol) of 7-chloro-9-methyl-2-phenyl-9H-imidazo[1,2-a]benzimidazole-3-acetic acid is prepared in 50 ml of dry tetrahydrofuran, 1.3 g (0.008 mol) of N,N'-carbonyldiimidazole are added thereto and the mixture is stirred at 40° C. for 2 h. The solution obtained is treated with an excess of dry gaseous methylamine and stirred for 72 h. The solvent is evaporated under reduced pressure. The residue is treated with 50 ml of water. The insoluble matter is separated by filtration, washed with water and then dried. 1.66 g of solid are obtained which are purified by silica gel chromatography, eluting with a dichloromethane/methanol 95/5 mixture. The product is recrystallized from an N,N-dimethylformamide/water 75/25 mixture and then dried. 1.27 g of solid are obtained. Melting point: 274°-275° C.

Workup

  1. customThe solution obtained
  2. stirringstirred for 72 h
  3. customThe solvent is evaporated under reduced pressure
  4. additionThe residue is treated with 50 ml of water
  5. customThe insoluble matter is separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-d97eb56fe3774610b576c1fcbe616ae1
Source dataset
uspto-grants-1995_11
Patent number
US05466706

Reaction notes

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