Morpholine → HCID 56849163, compound

HRID 1844846Notes

Reaction equation

HRID 1844846 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].[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.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>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:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]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 8083MorpholineHCID 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 56849163HCID 56849163, compoundYield 77.9%

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) (0.432 g, about 0.972 mmol), morpholine (0.11 mL, 1.263 mmol), DIEA (0.18 mL, 1.04 mmol) and HATU (0.342 g, 0.899 mmol) were added to a mixed solvent of DMF (4.5 mL) and dichloromethane (4.5 mL). The mixture was stirred at room temperature for 7 hr. Water and ethyl acetate were added. The mixture was extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to produce a crude yellow solid, which was washed with methanol and ethyl ether to produce a purified product (0.371 g) in 77.9% yield.

Workup

  1. customIn a dried reaction flask
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customto produce a crude yellow solid, which
  7. washwas washed with methanol and ethyl ether

Sources & evidence

ORD record
ord-c722f97405b84c6abea0fec31de75388
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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