HCID 24762728, compound → HCID 59129440, compound

HRID 1404036Notes

Reaction equation

HRID 1404036 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[C:23]([C:25]#[N:26])[CH:24]=4)[NH:21][C:20]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:26][CH2:25][C:23]1[CH:24]=[C:16]([NH:15][C:13]([C:10]2([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[CH2:11][CH2:12]2)=[O:14])[CH:17]=[C:18]2[C:22]=1[NH:21][C:20]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:19]2

Participants

5

Reactant 2

HCID 24762728HCID 24762728, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59129440HCID 59129440, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-7-cyano-1H-indol-5-yl)cyclopropanecarboxamide (375 mg, 0.934 mmol) was dissolved in 35 mL of ethyl acetate. The solution was recirculated through a continuous flow hydrogenation reactor containing 10% palladium on carbon at 100° C. under 100 bar of hydrogen for 8 h. The crude product was then evaporated to dryness and purified on 12 g of silica gel utilizing a gradient of 0-100% ethyl acetate (containing 0.5% triethylamine) in hexanes to yield N-(7-(aminomethyl)-2-tert-butyl-1H-indol-5-yl)-1-(benzo[d][1,3]-dioxol-5-yl)-cyclopropanecarboxamide (121 mg, 32%). ESI-MS m/z calc. 405.2, found 406.5 (M+1)+. Retention time of 1.48 minutes.

Workup

  1. customThe solution was recirculated through a continuous flow hydrogenation reactor
  2. customThe crude product was then evaporated to dryness
  3. custompurified on 12 g of silica gel utilizing a gradient of 0-100% ethyl acetate (containing 0.5% triethylamine) in hexanes

Sources & evidence

ORD record
ord-0d97d1e9b3354a0caca084d1a9c9454e
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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