Diisopropylethylamine → 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(1-(diphenylmethyl)azetidin-3-yl)-1H-1,2,3-triazol-4-yl)-2-aminopyridine

HRID 1845891Notes

Reaction equation

HRID 1845891 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:21])=[N:15][CH:16]=[C:17]([C:19]#[CH:20])[CH:18]=1)[CH3:11].C(N(C(C)C)CC)(C)C.[C:31]1([CH:37]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[N:38]2[CH2:41][CH:40]([N:42]=[N+:43]=[N-:44])[CH2:39]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CO.[Cu](I)I>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:21])=[N:15][CH:16]=[C:17]([C:19]2[N:44]=[N:43][N:42]([CH:40]3[CH2:41][N:38]([CH:37]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[CH2:39]3)[CH:20]=2)[CH:18]=1)[CH3:11]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 155126523-Azido-1-benzhydrylazetidineHCID 897084823-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)-5-ethynyl-2-aminopyridine

Product 1

HCID 897084703-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(1-(diphenylmethyl)azetidin-3-yl)-1H-1,2,3-triazol-4-yl)-2-aminopyridine

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 887MethanolSolvent

Procedure

The compound 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-ethynyl-2-aminopyridine (4.2 g, 12.62 mmol) was dissolved in methanol (40 mL), and diisopropylethylamine (8.36 g, 64.78 mmol), copper iodide (62 mg, 0.33 mmol) and 1-(diphenylmethyl)-3-azidoazetidine (3.34 g, 12.62 mmol) were added successively. The reaction was stirred overnight at room temperature. TLC test showed that the raw materials were completely reacted. The resultant mixture was concentrated under reduced pressure;

Workup

  1. customwere completely reacted
  2. concentrationThe resultant mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b076a9776af34b5687b4bff2415888a9
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

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