Phenylglyoxylic Acid → HCID 22479873, compound

HRID 2183313Notes

Reaction equation

HRID 2183313 reaction equation
[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=O.Cl.CN(C)CCCN=C=NCC.[O:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[N:30]1[C:38]2[C:33](=[CH:34][C:35]([C:39]3[N:43]=[CH:42][N:41]([C:44]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:40]=3)=[CH:36][CH:37]=2)[C:32]([C:63]2[CH:64]=[C:65]([NH2:69])[CH:66]=[CH:67][CH:68]=2)=[N:31]1>ClCCl>[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([NH:69][C:65]1[CH:66]=[CH:67][CH:68]=[C:63]([C:32]2[C:33]3[C:38](=[CH:37][CH:36]=[C:35]([C:39]4[N:43]=[CH:42][N:41]([C:44]([C:45]5[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=5)([C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)[C:57]5[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=5)[N:40]=4)[CH:34]=3)[N:30]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][O:24]3)[N:31]=2)[CH:64]=1)=[O:5]

Participants

5

Reactant 3

HCID 11915Phenylglyoxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 211011823-(1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine

Product 1

HCID 22479873HCID 22479873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-oxo-2-phenylacetic acid (0.074 g, 0.498 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 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. After 2 days at room temperature, the reaction was not complete. Another 2 equivalents of EDCI were added to the mixture, driving the reaction to completion within 12 hours. 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) 735 [M+H]+.

Workup

  1. additionwas added
  2. customthe reaction to completion within 12 hours
  3. customThe reaction mixture was then partitioned between dichloromethane and water

Sources & evidence

ORD record
ord-4024a3a64e164be2a9c8d19a3a830bae
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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