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

HRID 505536노트

반응식

HRID 505536 반응식
[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

참가 물질

6

반응물 3

HCID 72402-ChloroanilineHCID 65578Oxalyl chlorideHCID 68428094[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetic acid

생성물 1

HCID 251097522-[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]-N-(2-chlorophenyl)acetamide

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0b4d63c05d45480794ebb89f3a08d135
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781454B2

반응 노트

불러오는 중…