Triethylamine → HCID 178492115, compound

HRID 1161532Notes

Reaction equation

HRID 1161532 reaction equation
[Cl-].[OH:2][NH3+:3].C(N(CC)CC)C.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH:20]([C:36]2[CH:46]=[C:45]([O:47][CH3:48])[C:39]3[O:40][CH2:41][CH2:42][CH2:43][O:44][C:38]=3[C:37]=2[F:49])[C:21]2[NH:25][C:24](=[O:26])[N:23]([C:27]3[N:35]=[CH:34][CH:33]=[CH:32][C:28]=3[C:29]([OH:31])=[O:30])[N:22]=2)=[CH:15][CH:14]=1)#[N:12]>CO>[F:49][C:37]1[C:38]2[O:44][CH2:43][CH2:42][CH2:41][O:40][C:39]=2[C:45]([O:47][CH3:48])=[CH:46][C:36]=1[CH:20]([NH:19][C:16]1[CH:15]=[CH:14][C:13]([C:11](=[NH:12])[NH:3][OH:2])=[CH:18][CH:17]=1)[C:21]1[NH:25][C:24](=[O:26])[N:23]([C:27]2[N:35]=[CH:34][CH:33]=[CH:32][C:28]=2[C:29]([OH:31])=[O:30])[N:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21645Hydroxylamine HClHCID 135982142HCID 135982142, compound

Product 1

HCID 178492115HCID 178492115, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

After adding 114 mg of hydroxylammonium chloride and 267 μl of triethylamine to a solution of 146 mg of 2-{3-[(4-cyanophenylamino)-(6-fluoro-9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}nicotinic acid in 10 ml of methanol, the mixture was heated for 28 hours at 60° C. After cooling the reaction mixture, it was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give the title compound (61 mg) as a light yellow solid.

Workup

  1. temperatureAfter cooling the reaction mixture, it
  2. customwas purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid)

Sources & evidence

ORD record
ord-bdfae69fb9464874a98e9dd7590ce298
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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