Carbamate → N1-Ethyl-5-((2-((pyrrolidin-1-ylcarbonyl)amino)-4-pyridyl)oxy)-1H-1-indolecarboxamide

HRID 2376862Notes

Reaction equation

HRID 2376862 reaction equation
N1CCCC1.C(=O)([O-])N.[CH2:10]([NH:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32]([N:34]4[CH2:39]C[CH:37](N5CCCC5)[CH2:36][CH2:35]4)=[O:33])[CH:26]=3)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=[O:14])[CH3:11]>CN(C)C=O>[CH2:10]([NH:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32]([N:34]4[CH2:39][CH2:37][CH2:36][CH2:35]4)=[O:33])[CH:26]=3)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 276CarbamateHCID 31268PyrrolidineHCID 9982436N1-Ethyl-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide

Product 1

HCID 11741289N1-Ethyl-5-((2-((pyrrolidin-1-ylcarbonyl)amino)-4-pyridyl)oxy)-1H-1-indolecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethylformamide (5 ml) and pyrrolidine (0.36 ml, 4.3 mmol) were added to a mixture (0.461 g) of phenyl N-(4-(1-(ethylamino)carbonyl)-1H-5-indolyl)oxy-2-pyridyl)carbamate and phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy)-2-pyridyl)-N-(phenoxycarbonyl)carbamate obtained in Example 77; the reaction mixture was stirred overnight; the reaction mixture was partitioned between ethyl acetate and water; and the organic layer was concentrated to yield the title compound as crystals (245 mg, 0.623 mmol).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. concentrationand the organic layer was concentrated

Sources & evidence

ORD record
ord-fff098fe31004b8b95ee757749e2d2f6
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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