Triethylamine → HCID 56849290, compound

HRID 1844851Notes

Reaction equation

HRID 1844851 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](O)=[O:29])=[N:17][C:18]=4[CH2:19][CH2:20]3)=[N:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].FC(F)(F)C(O)=O.[CH3:38][S:39]([CH2:42][CH2:43][NH2:44])(=[O:41])=[O:40].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(N(CC)CC)C>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]([NH:44][CH2:43][CH2:42][S:39]([CH3:38])(=[O:41])=[O:40])=[O:29])=[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

8

Reactant 5

HCID 8471TriethylamineHCID 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×HCID 86700926HCID 86700926, compound

Product 1

HCID 56849290HCID 56849290, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

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), the crude 2-(methylsulfonyl)ethylamine trifluoroacetate (1.258 g, about 4.06 mmol), DIEA (0.86 mL, 4.97 mmol), HATU (1.742 g, 4.581 mmol) and triethylamine (1.08 mL, 7.743 mmol) were added a mixed solvent of DMF (4.5 mL) and dichloromethane (4.5 mL). The mixture was stirred at room temperature for 24 hr, and was concentrated at reduced pressure. Water was added to the residue and the mixture was filtered to produce a crude yellow solid, which was then washed with methanol to produce a purified product (0.378 g) in 79.8% yield.

Workup

  1. customIn a dried reaction flask
  2. concentrationwas concentrated at reduced pressure
  3. additionWater was added to the residue
  4. filtrationthe mixture was filtered
  5. customto produce a crude yellow solid, which
  6. washwas then washed with methanol

Sources & evidence

ORD record
ord-cf7a45ab483c4ed2808833b0b633097d
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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