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 1272938Notes

Reaction equation

HRID 1272938 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-4e36d8b81b1c48eb93f6dfcb08ee1b6a
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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