Cyclopropanecarboxylic acid → HCID 131724917, compound

HRID 1353861Notes

Reaction equation

HRID 1353861 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[N:25]1[C:33]2[C:28](=[CH:29][C:30]([C:34]3[N:38]=[CH:37][N:36]([C:39]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[N:35]=3)=[CH:31][CH:32]=2)[C:27]([C:58]2[CH:59]=[C:60]([NH2:64])[CH:61]=[CH:62][CH:63]=2)=[N:26]1>ClCCl>[CH:1]1([C:4]([NH:64][C:60]2[CH:61]=[CH:62][CH:63]=[C:58]([C:27]3[C:28]4[C:33](=[CH:32][CH:31]=[C:30]([C:34]5[N:38]=[CH:37][N:36]([C:39]([C:40]6[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=6)([C:46]6[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=6)[C:52]6[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=6)[N:35]=5)[CH:29]=4)[N:25]([CH:20]4[CH2:21][CH2:22][CH2:23][CH2:24][O:19]4)[N:26]=3)[CH:59]=2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 15655Cyclopropanecarboxylic acidHCID 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 131724917HCID 131724917, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cyclopropanecarboxylic acid (0.024 g, 0.274 mmol) in 2.5 mL of dichloromethane was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.057 g, 0.298 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 (0.150 g, 0.248 mmol), dissolved in 1 mL of dichloromethane was added to the solution. The reaction was stirred at room temperature for 2 days while 2 additions of one equivalent of reagents were necessary. 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) 672 [M+H]+.

Workup

  1. additionwas added to the solution
  2. customThe reaction mixture was then partitioned between water and dichloromethane

Sources & evidence

ORD record
ord-8aafff51a43f4401879dd58f9f63213d
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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