Water → HCID 117778016, compound

HRID 1500507Notes

Reaction equation

HRID 1500507 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][O:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([NH2:22])=[N:20][CH:21]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][O:24][C:25](=[O:31])[CH2:26][CH2:27][C:28](O)=[O:29].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.O>CN(C)C=O.C(N(CC)C(C)C)(C)C>[O:29]=[C:28]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)=[CH:21][N:20]=1)[CH2:27][CH2:26][C:25]([O:24][CH3:23])=[O:31]

Participants

7

Reactant 4

HCID 962WaterHCID 77487monoMethyl succinateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117778047HCID 117778047, compound

Product 1

HCID 117778016HCID 117778016, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-[(4-phenylphenyl)methoxymethyl]pyridin-2-amine (0.189 g) in N,N-dimethylformamide (6.0 mL), N,N-diisopropylethylamine (0.453 mL), 4-methoxy-4-oxobutanoic acid (0.174 g), and 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.376 g) were added at room temperature, and the mixture was stirred at 80° C. for 2 hours. The reaction solution was cooled to room temperature, and water was then added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column (Yamazen Corporation, elution solvent: dichloromethane/ethyl acetate) to obtain the title compound (0.171 g).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by chromatography on a silica gel column (Yamazen Corporation, elution solvent: dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-2da95f29c97c4225aca8081fed550e4a
Source dataset
uspto-grants-2015_12
Patent number
US09206168B2

Reaction notes

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