Ammonia → HCID 45381320, compound

HRID 1402820Notes

Reaction equation

HRID 1402820 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([CH:7]2[CH2:15][C:14](=[O:16])[N:13]3[C:9](=[N:10][C:11]4[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:12]=43)[CH2:8]2)=[CH:3][CH:2]=1.C1(C2C=CC=CC=2)C=CC(C2CC(=O)N3C(=[N:37]C4C=CC(I)=CC=43)C2)=CC=1.N>O1CCOCC1.O>[C:1]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:6]=[CH:5][C:4]([CH:7]([CH2:8][C:9]2[NH:10][C:11]3[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:12]=3[N:13]=2)[CH2:15][C:14]([NH2:37])=[O:16])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 222Ammonia2×HCID 66759252HCID 66759252, compoundHCID 66760027HCID 66760027, compound

Product 1

HCID 45381320HCID 45381320, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The 1:1-mixture of 3-(biphenyl-4-yl)-7-iodo-3,4-dihydropyrido[1,2-a]benzimidazol-1(2H)-one and 3-(biphenyl-4-yl)-8-iodo-3,4-dihydropyrido[1,2-a]benzimidazol-1(2H)-one (140 mg) was dissolved in 1,4-dioxane (2 ml) at reflux temperature. A 25% solution of ammonia in water (1 ml) was added and refluxing was continued for 2 h while addition of 25% ammonia solution in 1 ml portions was repeated every half an hour (3 times). Then all volatiles were removed at the water aspirator and the residue was triturated with acetone to leave 3-(biphenyl-4-yl)-4-(5-iodo-2-benzimidazolyl)-butyramide (85 mg) as light colourless solid.

Workup

  1. temperatureat reflux temperature
  2. temperaturerefluxing
  3. waitwas repeated every half an hour
  4. customThen all volatiles were removed at the water aspirator
  5. customthe residue was triturated with acetone

Sources & evidence

ORD record
ord-4fe8e48336174895a019c4dfd0bf9c1f
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

Loading…