2-Chloronicotinic acid → HCID 10164230, compound

HRID 1348930Notes

Reaction equation

HRID 1348930 reaction equation
[C:1]([N:4]1[C:13]2[CH:12]=[CH:11][C:10]([NH2:14])=[CH:9][C:8]=2[C:7]2[N:15]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[N:16]=[C:17]([C:18]([NH2:20])=[O:19])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2].[Cl:28][C:29]1[N:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](O)=[O:32].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([N:4]1[C:13]2[CH:12]=[CH:11][C:10]([NH:14][C:31]([C:30]3[C:29]([Cl:28])=[N:37][CH:36]=[CH:35][CH:34]=3)=[O:32])=[CH:9][C:8]=2[C:7]2[N:15]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[N:16]=[C:17]([C:18]([NH2:20])=[O:19])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 762582-Chloronicotinic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9969088HCID 9969088, compound

Product 1

HCID 10164230HCID 10164230, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title material from Example 24 (1.2 g, 0.0033 mol) and 2-chloro-nicotinic acid (517 mg, 0.0033 mol) were combined, under argon, in 5 mL of DMF. Diisopropyl ethyl amine (862□L, 0.00495 mol) and HATU (1.88 g, 0.00495 mol) were added and the reaction was stirred for 18 hours at room temperature. The reaction was then concentrated in vacuo, and the resulting solids were triturated with water and isolated by vacuum filtration to give the product as an off white solid. 652 mg. (MW=504.91, 39% yield). LC/MS m/z=505.7 (m+1).

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. customthe resulting solids were triturated with water
  3. customisolated by vacuum filtration
  4. customto give the product as an off white solid

Sources & evidence

ORD record
ord-9887732230484e948925c358fa94265a
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

Loading…