2-Furylglyoxylic acid → 2-(2-Furyl)-2-oxo-N-(3-{1-perhydro-2H-pyran-2-yl-5 [1-(triphenylmethyl)(1,2,4-triazol-3-yl)] (1H-indazol-3-yl)} phenyl)acetamide

HRID 1353871Notes

Reaction equation

HRID 1353871 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[C:7]([OH:9])=O.Cl.CN(C)CCCN=C=NCC.[O:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[N:29]1[C:37]2[C:32](=[CH:33][C:34]([C:38]3[N:42]=[CH:41][N:40]([C:43]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[N:39]=3)=[CH:35][CH:36]=2)[C:31]([C:62]2[CH:63]=[C:64]([NH2:68])[CH:65]=[CH:66][CH:67]=2)=[N:30]1>ClCCl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[C:7]([NH:68][C:64]1[CH:65]=[CH:66][CH:67]=[C:62]([C:31]2[C:32]3[C:37](=[CH:36][CH:35]=[C:34]([C:38]4[N:42]=[CH:41][N:40]([C:43]([C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=5)([C:50]5[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=5)[C:56]5[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=5)[N:39]=4)[CH:33]=3)[N:29]([CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][O:23]3)[N:30]=2)[CH:63]=1)=[O:9]

Participants

5

Reactant 3

HCID 738462-Furylglyoxylic 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 224802062-(2-Furyl)-2-oxo-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-(2-furyl)-2-oxoacetic acid (0.070 g, 0.496 mmol) in 2.0 mL of dichloromethane, was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) as a solid (0.098 g, 0.510 mmol). The solution was stirred at room temperature for 15 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. The reaction was stirred at room temperature overnight. The reaction mixture was then partitioned between dichloromethane and water. The crude material that was obtained from evaporation of the extracts was not purified further. (Yield not calculated) ES-MS (m/z) 725 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-206772e3df404e9ab0e1ced7c373f501
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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