Triethylamine → HCID 59129283, compound

HRID 468444Notes

Reaction equation

HRID 468444 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([OH:15])=O)[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.S(Cl)(Cl)=O.CCN(CC)CC.[NH2:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32]([C:37]([CH3:43])([CH3:42])[CH2:38][CH2:39][C:40]#[N:41])=[CH:31]2>ClCCl.CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:27][C:28]4[CH:29]=[C:30]5[C:34](=[CH:35][CH:36]=4)[NH:33][C:32]([C:37]([CH3:43])([CH2:38][CH2:39][C:40]#[N:41])[CH3:42])=[CH:31]5)=[O:15])[CH2:11][CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl Chloride2×HCID 143496081-(1,3-Dioxaindan-5-yl)cyclopropane-1-carboxylic acidHCID 59129251HCID 59129251, compound

Product 1

HCID 59129283HCID 59129283, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxylic acid (0.068 g, 0.33 mmol) was added thionyl chloride (72 μL, 0.99 mmol) and DMF (20 μL) at room temperature. The mixture was stirred for 30 minutes before the excess thionyl chloride was evaporated under reduced pressure. To the resulting acid chloride, dichloromethane (0.5 mL) and Et3N (230 μL, 1.7 mmol) were added. A solution of 4-(5-amino-1H-indol-2-yl)-4-methylpentanenitrile (0.33 mmol) in dichloromethane (0.5 mL) was added to the acid chloride solution and the mixture was stirred at room temperature for 1.5 h. The resulting mixture was diluted with dichloromethane and washed with 1 N HCl (2×2 mL), saturated aqueous NaHCO3 (2×2 mL) and brine (2×2 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to give 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-(4-cyano-2-methylbutan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide.

Workup

  1. customwas evaporated under reduced pressure
  2. washwashed with 1 N HCl (2×2 mL), saturated aqueous NaHCO3 (2×2 mL) and brine (2×2 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0705dbdb9b5848918cf3bf9661560452
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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