2-Chloroaniline → 2-[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]-N-(2-chlorophenyl)acetamide

HRID 505536Notes

Reaction equation

HRID 505536 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([CH2:9][C:10]([OH:12])=O)[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.[Cl:31][C:32]1[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=1[NH2:34]>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:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[Cl:31])=[O:12])[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 72402-ChloroanilineHCID 65578Oxalyl chlorideHCID 68428094[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetic acid

Product 1

HCID 251097522-[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]-N-(2-chlorophenyl)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). This was followed by addition of DMF (1 drop) and then, following bubbling cessation, by addition of 2-chloroaniline (158 mg, 1.239 mmol). After 10 minutes, the reaction mixture was concentrated, taken up in DMF/MeOH and purified by reverse phase chromatography, eluting with 30-95% MeCN/H2O+0.1% TFA. The product fraction was lyophilized to yield the title compound. 1H NMR (DMSO-d6) δ 10.2 (s, 1H), 7.90 (d, J=9.0 Hz, 1H), 7.83 (m, 2H), 7.75 (d, J=8.3 Hz, 1H), 7.55 (m, 3H), 7.34 (m, 1H), 7.24 (m, 1H), 5.85 (s, 2H). HRMS (M+1)=472.0152.

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-0b4d63c05d45480794ebb89f3a08d135
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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