Pyrrolidine → HCID 10363908, compound

HRID 2376865Notes

Reaction equation

HRID 2376865 reaction equation
N1CCCC1.C1(NC(N2C3C(=CC(OC4C=CN=C(N(C(OC5C=CC=CC=5)=O)C(=O)OC5C=CC=CC=5)C=4)=CC=3)C=C2)=O)CC1.[CH:47]1([NH:50][C:51]([N:53]2[C:61]3[C:56](=[CH:57][C:58]([O:62][C:63]4[CH:68]=[CH:67][N:66]=[C:65]([NH:69][C:70]([N:72]5[CH2:77][CH2:76][CH:75](N6CCCC6)[CH2:74]C5)=[O:71])[CH:64]=4)=[CH:59][CH:60]=3)[CH:55]=[CH:54]2)=[O:52])[CH2:49][CH2:48]1>CN(C)C=O>[CH:47]1([NH:50][C:51]([N:53]2[C:61]3[C:56](=[CH:57][C:58]([O:62][C:63]4[CH:68]=[CH:67][N:66]=[C:65]([NH:69][C:70]([N:72]5[CH2:77][CH2:76][CH2:75][CH2:74]5)=[O:71])[CH:64]=4)=[CH:59][CH:60]=3)[CH:55]=[CH:54]2)=[O:52])[CH2:49][CH2:48]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 10435600HCID 10435600, compoundHCID 21949133HCID 21949133, compound

Product 1

HCID 10363908HCID 10363908, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethylformamide (5 ml) and pyrrolidine (0.35 ml, 4.2 mmol) were added to a mixture (470 mg) of phenyl N-(4-(1-cyclopropylaminocarbonyl-1H-5-indolyl)oxy-2-pyridyl)-N-(phenoxycarbonyl)carbamate and phenyl N-(4-(1-cyclopropylaminocarbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate obtained in Example 68; 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 white crystals (200 mg, 0.49 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-57a53604d7e445838c95e85ca5fe9696
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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