Oxalyl chloride → 2-[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]-N-[3-(trifluoromethyl)pyridin-4-yl]acetamide

HRID 505537Notes

Reaction equation

HRID 505537 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([CH2:9][C:10](O)=[O:11])[N:7]=[N:8][C:4]=2[C:3]=1[O:15][C:16]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([Cl:24])[CH:17]=1.C(Cl)(=O)C(Cl)=O.[F:31][C:32]([F:41])([F:40])[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][C:38]=1[NH2:39]>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([CH2:9][C:10]([NH:39][C:38]3[CH:37]=[CH:36][N:35]=[CH:34][C:33]=3[C:32]([F:41])([F:31])[F:40])=[O:11])[N:7]=[N:8][C:4]=2[C:3]=1[O:15][C:16]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([Cl:24])[CH:17]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 27828104-Amino-3-(trifluoromethyl)pyridineHCID 68428094[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetic acid

Product 1

HCID 251097532-[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]-N-[3-(trifluoromethyl)pyridin-4-yl]acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of [5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetic acid (15 mg, 0.041 mmol) (see step 2 in Example 16) in DCM (0.5 mL) was added oxalyl chloride (58 mg, 0.454 mmol), followed by addition of DMF (1 drop) and then, following bubbling cessation, by addition of 3-(trifluoromethyl)pyridin-4-amine (201 mg, 1.239 mmol). After 10 minutes, the reaction mixture was concentrated, taken up in MeOH/DMSO, and purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. Product fractions were lyophilized to yield the title compound. 1H NMR (CDCl3) δ 8.1 (m, 3H), 8.50 (s, 1H), 7.75 (d, J=8.8 Hz, 1H), 7.49 (d, J=8.8 Hz, 1H), 7.55 (m, 2H), 7.41 (m, 1H), 7.27 (m, 1H), 7.07 (s, 1H), 5.60 (s, 2H). HRMS (M+1)=507.0363

Workup

  1. customfollowing bubbling cessation
  2. concentrationthe reaction mixture was concentrated
  3. custompurified by reverse phase chromatography
  4. washeluting with 30-95% MeCN/H2O+0.1% TFA

Sources & evidence

ORD record
ord-278b07da926342d9938821a1d5f5efa6
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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