Triethylamine → HCID 58503938, compound

HRID 2407802Notes

Reaction equation

HRID 2407802 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([C:11]([OH:13])=O)[CH:3]=1.Cl.Cl.Cl.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[S:25][C:26]([CH2:29][N:30]2[CH2:35][CH2:34][CH:33]([CH2:36][NH2:37])[CH2:32][CH2:31]2)=[CH:27][N:28]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([C:11]([NH:37][CH2:36][CH:33]2[CH2:34][CH2:35][N:30]([CH2:29][C:26]3[S:25][C:24]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[F:17])=[N:28][CH:27]=3)[CH2:31][CH2:32]2)=[O:13])[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 66989510HCID 66989510, compoundHCID 714642104-Amino-6-chloro-5-cyanopicolinic acid

Product 1

HCID 58503938HCID 58503938, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,1′-carbodiimidazole (0.15 g) and 4-amino-6-chloro-5-cyanopicolinic acid (0.14 g, prepared according to the reported preparation in Zhao, Hongyu, et al.; J. Med. Chem. 2006, 49(15), 4455-4458) in N,N-dimethylformamide (3.5 mL) was stirred one hour at room temperature. The compound prepared in Example 392 (0.30 g) and triethylamine (0.60 mL) were added and the reaction was stirred for one hour more. A saturated sodium bicarbonate solution was added and the mixture was vigorously stirred overnight. The mixture was diluted with water and then filtered. The solids were evaporated from acetone and then a 1:1 dichloromethane:toluene solution. The solids were triturated with dichloromethane to furnish the title compound (0.22 g) having the following physical data.

Workup

  1. customaccording to the reported preparation in Zhao, Hongyu, et al.
  2. waitthe mixture was vigorously stirred overnight
  3. filtrationfiltered
  4. customThe solids were evaporated from acetone
  5. customThe solids were triturated with dichloromethane

Sources & evidence

ORD record
ord-fe0e4f048e2a4e4e9429cdb28c10e214
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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