Ammonia → HCID 19955602, compound

HRID 1779439Notes

Reaction equation

HRID 1779439 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[C:28](=O)[C:29](=[O:35])[C:30]=3[O:31]C(C)C)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[NH3:37]>>[NH2:37][C:28]1[C:29](=[O:35])[C:30](=[O:31])[C:27]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:13]2[C:6]3=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]3[N:4]=[C:3]2[CH2:1][CH3:2])=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 19955587HCID 19955587, compound

Product 1

HCID 19955602HCID 19955602, compound

Procedure

3-[4'-(2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyrid-3-ylmethyl)biphenyl-2-yl)-4-isopropoxycyclobut-3-ene-1,2-dione (0.44 g; preparable as in Example 2) was stirred in saturated ethanolic ammonia solution (10 ml) at ambient temperature for 3 hours and then kept at ambient temperature for approximately 16 hours. The solvent was evaporated and the resulting residue was triturated with diethyl ether to give an off-white solid which was dried in vacuo to give 3-amino-4-[4'-(2-ethyl-5,7-dimethyl -3H-imidazo[4,5-b]pyrid-3-ylmethyl)biphenyl-2-yl]cyclobut-3-ene-1,2-dione (0.25g; m.p. 217° C.), an active compound of the present invention.

Workup

  1. customThe solvent was evaporated
  2. customthe resulting residue was triturated with diethyl ether
  3. customto give an off-white solid which
  4. customwas dried in vacuo

Sources & evidence

ORD record
ord-861e651c5ebf466ba08497395f2fcf2d
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

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