Water → HCID 86618291, compound

HRID 2264608Notes

Reaction equation

HRID 2264608 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[C:26](Cl)[N:25]=[CH:24][N:23]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[N-:31]=[N+:32]=[N-:33].[Na+].O>CN(C=O)C>[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[C:26]([N:31]=[N+:32]=[N-:33])[N:25]=[CH:24][N:23]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 58659388HCID 58659388, compound

Product 1

HCID 86618291HCID 86618291, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4.70 g (10.8 mMol) 5-(6-chloro-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide (WO 03/099771; Ex. 163) in 50 ml DMF, 1.4 g (21.6 mMol) NaN3 are added at rt. Then the mixture is stirred for 3 h at 70° C., cooled to rt and pored into water and extracted tree times with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated, yielding the title compound: m.p.: 167-168° C.

Workup

  1. temperaturecooled to rt
  2. extractionextracted tree times with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-21860cc01642434f974dba010ab83b92
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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