1,2-Dichloroethane → HCID 24763146, compound

HRID 1964391Notes

Reaction equation

HRID 1964391 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([CH3:22])([CH3:21])[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:5]2.[O:23]1[C:27]2[CH:28]=[C:29]([C:32]3([C:35](O)=[O:36])[CH2:34][CH2:33]3)[CH:30]=[CH:31][C:26]=2[O:25][CH2:24]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.O>[O:25]1[C:26]2[CH:31]=[CH:30][C:29]([C:32]3([C:35]([NH:1][C:2]4[CH:3]=[C:4]5[C:8](=[CH:9][CH:10]=4)[NH:7][C:6]([C:11]([CH3:22])([CH3:21])[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[CH:5]5)=[O:36])[CH2:33][CH2:34]3)=[CH:28][C:27]=2[O:23][CH2:24]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 143496081-(1,3-Dioxaindan-5-yl)cyclopropane-1-carboxylic acidHCID 59129351HCID 59129351, compound

Product 1

HCID 24763146HCID 24763146, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 2-(5-amino-1H-indol-2-yl)-2-methylpropylcarbamate (58 mg, 0.19 mmol), 1-(benzo[d][1,3]dioxol-6-yl)cyclopropanecarboxylic acid (47 mg, 0.23 mmol), EDC (45 mg, 0.23 mmol), HOBt (31 mg, 0.23 mmol) and Et3N (80 μL, 0.57 mmol) were dissolved in DMF (4 mL) and stirred overnight at room temperature. The mixture was diluted with water and extracted with ethylacetate. The combined organic phases were dried over magnesium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography (10-30% ethylacetate in hexane) to give tert-butyl 2-(5-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-1H-indol-2-yl)-2-methylpropyl-carbamate (88 mg, 94%). 1H NMR (400 MHz, CDCl3) δ 8.32 (s, 1H), 7.62 (d, J=1.5 Hz, 1H), 7.18-7.16 (m, 2H), 7.02-6.94 (m, 3H), 6.85 (d, J=7.8 Hz, 1H), 6.19 (d, J=1.5 Hz, 1H), 6.02 (s, 2H), 4.54 (m, 1H), 3.33 (d, J=6.2 Hz, 2H), 1.68 (dd, J=3.7, 6.8 Hz, 2H), 1.36 (s, 9H), 1.35 (s, 6H), 1.09 (dd, J=3.7, 6.8 Hz, 2H).

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by silica gel chromatography (10-30% ethylacetate in hexane)

Sources & evidence

ORD record
ord-176cd3f97d8440e09497cb9e95f7e54c
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

Loading…