Dimethylamine, hydrochloride → HCID 56849103, compound

HRID 1844843Notes

Reaction equation

HRID 1844843 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].Cl.[CH3:32][NH:33][CH3:34].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>O.ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:22]([CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[CH:21]3[C:12]([C:13]4[CH:14]=[CH:15][C:16]([C:28]([N:33]([CH3:34])[CH3:32])=[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

8

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531Diisopropylethylamine2×HCID 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 56849103HCID 56849103, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 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), dimethylamine hydrochloride (0.095 g, 1.17 mmol), DIEA (N,N-diisopropylethylamine, the same below) (0.18 mL, 1.04 mmol) and HATU (2-(7-azobenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, the same below) (0.342 g, 0.899 mmol) were added to a mixed solvent of DMF (dimethylformamide) (6.5 mL) and dichloromethane (6.5 mL). The mixture was stirred at room temperature for 3 hr and water was added.

Workup

  1. customIn a dried reaction flask

Sources & evidence

ORD record
ord-af48eccde9454a65b9173c64e9a3e6d8
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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