HCID 11665716, compound → HCID 58117360, compound

HRID 1406408Notes

Reaction equation

HRID 1406408 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[C:18](=[O:33])[N:19]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:20]([CH3:24])=[C:21]([NH2:23])[CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:34][C:35]1[CH:36]=[C:37]([CH:47]=[CH:48][CH:49]=1)[CH2:38][N:39]1[CH:43]=[C:42]([C:44](O)=[O:45])[CH:41]=[N:40]1.FC1C=CC(CN2C=C(C(O)=O)C=N2)=CC=1>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[C:18](=[O:33])[N:19]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[C:20]([CH3:24])=[C:21]([NH:23][C:44]([C:42]2[CH:41]=[N:40][N:39]([CH2:38][C:37]3[CH:47]=[CH:48][CH:49]=[C:35]([F:34])[CH:36]=3)[CH:43]=2)=[O:45])[CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 11665716HCID 11665716, compoundHCID 43565332HCID 43565332, compoundHCID 58117460HCID 58117460, compound2×

Product 1

HCID 58117360HCID 58117360, compound

Procedure

The title compound was prepared according to the experimental used in Example 20, Step 4 with intermediate (7d), 2-[5-amino-6-methyl-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydropyridin-3-yl]indole-1-carboxylic acid tert-butyl ester, and 1-(3-Fluoro-benzyl)-1H-pyrazole-4-carboxylic acid, which was synthesised according to the protocol described for intermediate (6e) in Example 21. The resultant crude product was purified by flash chromatography on SiO2 with hexane—50% ethyl acetate/hexane (gradient) to afford the title compound as a yellow oil, 80 mg, 70%.

Workup

  1. customThe title compound was prepared
  2. customwas synthesised
  3. customThe resultant crude product was purified by flash chromatography on SiO2 with hexane—50% ethyl acetate/hexane (gradient)

Sources & evidence

ORD record
ord-3e9c65bde68e47d8a49010aa78f2f86c
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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