Dimethylformamide → HCID 10364778, compound

HRID 2215542Notes

Reaction equation

HRID 2215542 reaction equation
CN(C)C=O.N1CCCCC1.C1(NC(N2C3C(=CC(OC4C=CN=C(NC(=O)OC5C=CC=CC=5)C=4)=CC=3)C=C2)=O)CC1.[CH:44]1([NH:47][C:48]([N:50]2[C:58]3[C:53](=[CH:54][C:55]([O:59][C:60]4[CH:65]=[CH:64][N:63]=[C:62]([NH:66][C:67]([N:69]5[CH2:74][CH2:73][CH:72](N6CCCC6)[CH2:71][CH2:70]5)=[O:68])[CH:61]=4)=[CH:56][CH:57]=3)[CH:52]=[CH:51]2)=[O:49])[CH2:46][CH2:45]1>C(OCC)C>[CH:44]1([NH:47][C:48]([N:50]2[C:58]3[C:53](=[CH:54][C:55]([O:59][C:60]4[CH:65]=[CH:64][N:63]=[C:62]([NH:66][C:67]([N:69]5[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]5)=[O:68])[CH:61]=4)=[CH:56][CH:57]=3)[CH:52]=[CH:51]2)=[O:49])[CH2:46][CH2:45]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 10435600HCID 10435600, compoundHCID 21949215HCID 21949215, compound

Product 1

HCID 10364778HCID 10364778, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N,N-Dimethylformamide (5 ml) and piperidine (0.42 ml, 4.2 mmol) were added to a mixture (467 mg) of phenyl N-(4-(1-cyclopropylaminocarbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate and phenyl N-(4-(1-cyclopropylaminocarbonyl-1H-5-indolyl)oxy-2-pyridyl)-N-(phenoxycarbonyl)carbamate obtained in Example 68; and the reaction mixture was stirred overnight; the reaction mixture was partitioned between ethyl acetate and water; the organic layer was concentrated; the obtained solid was washed with a solvent mixture of hexane:diethyl ether=1:1 to yield the title compound as crystals (241 mg, 0.57 mmol).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. concentrationthe organic layer was concentrated
  3. washthe obtained solid was washed with a solvent mixture of hexane

Sources & evidence

ORD record
ord-e37a92e3050c42a2833fd45c62190408
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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