Piperidin-4-ol → HCID 56849226, compound

HRID 1844847Notes

Reaction equation

HRID 1844847 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:22]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:21]3[C:12]([C:13]4[CH:14]=[CH:15][C:16]([C:28]([OH:30])=O)=[N:17][C:18]=4[CH2:19][CH2:20]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:64][CH:65]1[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]1>C(OCC)(=O)C.O.ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:22]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:21]3[C:12]([C:13]4[CH:14]=[CH:15][C:16]([C:28]([N:68]5[CH2:69][CH2:70][CH:65]([OH:64])[CH2:66][CH2:67]5)=[O:30])=[N:17][C:18]=4[CH2:19][CH2:20]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

9

Reactant 4

HCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 56849102HCID 56849102, compound2×

Product 1

HCID 56849226HCID 56849226, compoundYield 47.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a dried reaction flask, the crude 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylic acid (Compound 1) (0.4 g, about 0.9 mmol), DIEA (0.5 mL, 2.89 mmol) and HATU (1.047 g, 2.754 mmol) were added to DMF (4.5 mL). To the mixture was added dropwise a solution of dichloromethane (9 mL) dissolved in 4-hydroxylpiperidine (0.446 g, 4.409 mmol) under an ice-salt bath. After the completion of the dropwise addition, the mixture was stirred at room temperature for 4 days. Water and ethyl acetate were added. The mixture was extracted with ethyl acetate. The combined organic phase was washed with water and saturated salt water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to produce a crude yellow solid, which were washed with ethyl ether and ethyl acetate respectively to produce a purified product (0.217 g) in 47.8% yield.

Workup

  1. customIn a dried reaction flask
  2. additionAfter the completion of the dropwise addition
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe combined organic phase was washed with water and saturated salt water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customto produce a crude yellow solid, which
  8. washwere washed with ethyl ether and ethyl acetate respectively

Sources & evidence

ORD record
ord-8ef81be73a794fa18ab7c230f50e8e79
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

Loading…