Triethylamine → HCID 59129283, compound

HRID 1908531Notes

Reaction equation

HRID 1908531 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-67516753693b4d0991462dd0a530d4e9
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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