1,2-Dichloroethane → HCID 24763146, compound

HRID 1404011Notes

Reaction equation

HRID 1404011 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 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-methylpropylcarbamate (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 and to dryness
  3. customThe residue was purified by silica gel chromatography (10-30% ethylacetate in hexane)

Sources & evidence

ORD record
ord-1521960d556742b98b71e6ff5d750544
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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