HCID 58117306, compound → HCID 58117226, compound

HRID 1406418Notes

Reaction equation

HRID 1406418 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:24]1[C:25](=[O:39])[N:26]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:27]=[C:28]([NH2:30])[CH:29]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:40][C:41]1[CH:55]=[CH:54][C:44]([CH2:45][N:46]2[CH:50]=[C:49]([C:51](Cl)=[O:52])[CH:48]=[N:47]2)=[CH:43][CH:42]=1>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:24]1[C:25](=[O:39])[N:26]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:38])[CH3:37])[CH:27]=[C:28]([NH:30][C:51]([C:49]2[CH:48]=[N:47][N:46]([CH2:45][C:44]3[CH:54]=[CH:55][C:41]([CH3:40])=[CH:42][CH:43]=3)[CH:50]=2)=[O:52])[CH:29]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 58117306HCID 58117306, compound2×HCID 86650204HCID 86650204, compound

Product 1

HCID 58117226HCID 58117226, compound

Procedure

The title compound was prepared by the route outlined in Scheme 10 and using the experimental from Example 115, Step 4, with intermediate (10e), 2-[5-amino-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridin-3-yl]-5-(4-methyl-piperazin-1-yl)-indole-1-carboxylic acid tert-butyl ester (0.1 g, 0.18 mmol) and 1-(4-methyl-benzyl)-1H-pyrazole-4-carbonyl chloride (0.047 g, 0.2 mmol). The resultant crude product was purified by flash chromatography on SiO2 eluting with dichloromethane—8% methanol/dichloromethane (gradient) to afford the desired title compound as a pale brown solid, 0.107 g, 79%.

Workup

  1. customThe title compound was prepared by the route
  2. customThe resultant crude product was purified by flash chromatography on SiO2 eluting with dichloromethane—8% methanol/dichloromethane (gradient)

Sources & evidence

ORD record
ord-eb9a86bdd6a84da69b78eb531c1d5c4e
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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