Hydrochloric Acid → HCID 68161482, compound

HRID 2041771Notes

Reaction equation

HRID 2041771 reaction equation
CC([CH2:5][N:6]([CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]([C:27](=[O:29])[CH3:28])[C@@H:22]([CH3:30])[CH2:21][C@H:20]3[NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][N:33]=2)[CH:14]=[N:13]1)C(=O)[O-])(C)C.FC(F)(F)C(O)=O.[ClH:46].CCOCC>ClCCl>[ClH:46].[C:27]([N:23]1[C:24]2[C:19](=[CH:18][C:17]([C:15]3[CH:14]=[N:13][N:12]([CH2:11][CH2:10][NH:6][CH3:5])[CH:16]=3)=[CH:26][CH:25]=2)[C@H:20]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][N:33]=2)[CH2:21][C@@H:22]1[CH3:30])(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 86669461HCID 86669461, compound

Product 1

HCID 68161482HCID 68161482, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl[2-(4-{(2S,4R)-1-acetyl-2-methyl-4-[(5-methyl-2-pyridinyl)amino]-1,2,3,4-tetrahydro-6-quinolinyl}-1H-pyrazol-1-yl)ethyl]methylcarbamate (for a preparation see intermediate 77) (40 mg, 0.077 mmol) in dichloromethane (DCM) (4 mL) was treated with trifluoroacetic acid (1 mL, 12.98 mmol) and the resulting mixture was stirred at room temperature for 3 h then concentrated in vacuo. The residue was loaded onto a 2 g SCX cartridge and eluted with MeOH (45 mL) followed by 2M NH3 in MeOH (45 mL). The ammonia fractions were combined and concentrated in vacuo. The residue was dissolved in MeOH (1 mL) and the solution was treated with HCl (1M in Et2O, 0.09 mmol, 0.09 ml) then was concentrated in vacuo. Trituration of the residue with Et2O gave (2S,4R)-1-acetyl-2-methyl-6-{-1-[2-(methylamino)ethyl]-1H-pyrazol-4-yl}-N-(5-methyl-2-pyridinyl)-1,2,3,4-tetrahydro-4-quinolinamine hydrochloride (39 mg, 0.073 mmol, 94%) as a beige solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. washeluted with MeOH (45 mL)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in MeOH (1 mL)
  5. concentrationthen was concentrated in vacuo

Sources & evidence

ORD record
ord-84a4124dc2be4e04a370e03436de70fd
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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