Benzyl azide → 6-(1-Benzyl-1H-1,2,3-triazol-4-yl)-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

HRID 1888606노트

반응식

HRID 1888606 반응식
[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[C:5]([C:10]2[C:11](F)=[N:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:18][CH:17]=3)[CH:15]=2)[CH:4]=1)#[CH:2].[N:30]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[N+:31]=[N-:32]>CN(C)C=O.C(Cl)Cl.CO.[Cu]I>[CH2:33]([N:30]1[CH:2]=[C:1]([C:3]2[N:8]=[CH:7][C:6]3[NH:9][C:11]4[N:12]=[CH:13][C:14]([C:16]5[CH:21]=[CH:20][C:19]([CH2:22][N:23]6[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]6)=[CH:18][CH:17]=5)=[CH:15][C:10]=4[C:5]=3[CH:4]=2)[N:32]=[N:31]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

참가 물질

7

반응물 2

HCID 12152Benzyl azideHCID 582664586'-Ethynyl-2-fluoro-5-(4-piperidin-1-ylmethylphenyl)-[3,4']bipyridinyl-3'-ylamine

생성물 1

HCID 445465526-(1-Benzyl-1H-1,2,3-triazol-4-yl)-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
60 °C

실험 절차

A mixture of 6′-ethynyl-2-fluoro-5-(4-piperidin-1-ylmethylphenyl)-[3,4′]bipyridinyl-3′-ylamine (60 mg, 0.16 mmol), copper (I) iodide (3.0 mg, 0.016 mmol), and azidomethylbenzene (29 mg, 0.22 mmol) in N,N-dimethylformamide (2 mL) was heated at 60° C. for 2 h. The cooled reaction mixture was diluted with DCM (20 mL) and methanol (2 mL) and washed with water (15 mL). The organic phase was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford a brown residue that was taken to the next step without purification.

후처리

  1. customThe cooled reaction mixture
  2. washwashed with water (15 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a brown residue that
  8. customwas taken to the next step without purification

출처 및 근거

ORD 기록
ord-d605445655f74aa5a8fe4edc152038db
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501765B2

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