Dimethylformamide → HCID 59374152, compound

HRID 473751Notes

Reaction equation

HRID 473751 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[CH:29]=[CH:28][C:17]([O:18][C:19]2[N:27]=[CH:26][CH:25]=[CH:24]C=2C(O)=O)=[CH:16][CH:15]=1.CN(C=O)C>C(Cl)Cl>[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[CH:29]=[CH:28][C:17]([O:18][C:19]2[N:27]=[CH:26][CH:25]=[CH:24][C:1]=2[C:2]([Cl:4])=[O:3])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 593739222-(4-(Pyridin-2-ylamino)phenoxy)nicotinic acid

Product 1

HCID 59374152HCID 59374152, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2M solution of oxaloyl chloride (3.86 mL, 7.71 mmol) was added slowly to a suspension of 2-(4-(pyridin-2-ylamino)phenoxy)nicotinic acid (1580 mg, 5.14 mmol) in CH2Cl2 (20 mL). DMF (0.040 mL, 0.514 mmol) was added drop wise and the mixture was stirred at RT for 2 h. The mixture was concentrated under reduced pressure to deliver a yellow solid. The solid was suspended in CH2Cl2 (5 ml) and filtered to deliver 2-(4-(pyridin-2-ylamino)phenoxy)nicotinoyl chloride as a yellow solid that was taken on without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. filtrationfiltered
  3. customwas taken on without further purification

Sources & evidence

ORD record
ord-bf26ff38178d4a9d8bea80c4f9136714
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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