Water → HCID 59129508, compound

HRID 1964439Notes

Reaction equation

HRID 1964439 reaction equation
N[CH2:2][C:3]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH:15][C:16]([C:18]1([C:21]3[CH:29]=[CH:28][C:24]4[O:25][CH2:26][O:27][C:23]=4[CH:22]=3)[CH2:20][CH2:19]1)=[O:17])=[CH:10][CH:9]=2)(C)[CH3:4].C(=O)([O-])[O-].[K+].[K+].IC.O.[CH3:39][N:40]([CH:42]=O)[CH3:41]>>[O:25]1[C:24]2[CH:28]=[CH:29][C:21]([C:18]3([C:16]([NH:15][C:11]4[CH:12]=[C:13]5[C:8](=[CH:9][CH:10]=4)[NH:7][C:6]([C:3]([CH3:4])([CH3:2])[CH2:42][N:40]([CH3:39])[CH3:41])=[CH:14]5)=[O:17])[CH2:20][CH2:19]3)=[CH:22][C:23]=2[O:27][CH2:26]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59129572HCID 59129572, compound

Product 1

HCID 59129508HCID 59129508, compoundYield 33%

Procedure

To a solution of N-(2-(1-amino-2-methylpropan-2-yl)-1H-indol-5-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (20 mg, 0.051 mmol) in DMF (1 mL) was added potassium carbonate (35 mg, 0.26 mmol) and iodomethane (7.0 μL, 0.11 mmol). The mixture was stirred for 2 h. Water was added and the mixture was extracted with dichloromethane. Combined organic phases were dried over magnesium sulfate, evaporated, coevaporated with toluene (3×) and purified by silica gel chromatography (0-30% EtOAc in hexane) to give 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-(1-(dimethylamino)-2-methylpropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide (7 mg, 33%). 1H NMR (400 MHz, CDCl3) δ 9.74 (s, 1H), 7.58 (d, J=1.9 Hz, 1H), 7.20 (d, J=8.6 Hz, 1H), 7.15 (s, 1H), 7.01-6.95 (m, 3H), 6.85 (d, J=7.9 Hz, 1H), 6.10 (d, J=0.9 Hz, 1H), 6.02 (s, 2H), 2.43 (s, 2H), 2.24 (s, 6H), 1.68 (dd, J=3.7, 6.7 Hz, 2H), 1.33 (s, 6H), 1.08 (dd, J=3.7, 6.8 Hz, 2H).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialCombined organic phases were dried over magnesium sulfate
  3. customevaporated
  4. custompurified by silica gel chromatography (0-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-593fa6277a5242c8865c0db090665aa9
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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