Triethylamine → 2-(Dimethylamino)-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)) phenyl)acetamide

HRID 2183292Notes

Reaction equation

HRID 2183292 reaction equation
Cl.[CH3:2][N:3]([CH3:8])[CH2:4][C:5](O)=[O:6].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[O:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[N:34]1[C:42]2[C:37](=[CH:38][C:39]([C:43]3[N:47]=[CH:46][N:45]([C:48]([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)[C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[N:44]=3)=[CH:40][CH:41]=2)[C:36]([C:67]2[CH:68]=[C:69]([NH2:73])[CH:70]=[CH:71][CH:72]=2)=[N:35]1>ClCCl>[CH3:2][N:3]([CH3:8])[CH2:4][C:5]([NH:73][C:69]1[CH:70]=[CH:71][CH:72]=[C:67]([C:36]2[C:37]3[C:42](=[CH:41][CH:40]=[C:39]([C:43]4[N:47]=[CH:46][N:45]([C:48]([C:49]5[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=5)([C:55]5[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=5)[C:61]5[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=5)[N:44]=4)[CH:38]=3)[N:34]([CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][O:28]3)[N:35]=2)[CH:68]=1)=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 75605N,N-Dimethylglycine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 211011823-(1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine

Product 1

HCID 224800272-(Dimethylamino)-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)) phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(dimethylamino)acetic acid hydrochloride (0.077 g, 0.55 mmol) in 5 mL of dichloromethane was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.105 g, 0.55 mmol) and triethyl amine (0.077 mL, 0.55 mmol). The reaction was stirred at room temperature for 10 min before 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine (0.300 g, 0.498 mmol), dissolved in 1 mL of dichloromethane was added to the solution. The reaction was stirred at room temperature overnight. Further conversion was promoted by reacting an additional equivalent of reagents and stirring at room temperature for 12 hours. The reaction mixture was then partitioned between water and dichloromethane. The crude material that was obtained from evaporation of the extracts was not purified further. (Yield not calculated) ES-MS (m/z) 688 [M+H]+.

Workup

  1. additionwas added to the solution
  2. stirringstirring at room temperature for 12 hours
  3. customThe reaction mixture was then partitioned between water and dichloromethane

Sources & evidence

ORD record
ord-0d2f7c04654748a5bc8893ab11e76c42
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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