Hydrochloric Acid → HCID 68161610, compound

HRID 2041773Notes

Reaction equation

HRID 2041773 reaction equation
C1(CO[C:9](=O)[N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[N:25]([C:29](=[O:31])[CH3:30])[C@@H:24]([CH3:32])[CH2:23][C@H:22]4[NH:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][N:35]=3)=[CH:15][CH:14]=2)C)C=CC=CC=1.[ClH:42]>C(O)C.CO.[Pd]>[ClH:42].[C:29]([N:25]1[C:26]2[C:21](=[CH:20][C:19]([C:16]3[CH:15]=[CH:14][C:13]([CH2:12][NH:10][CH3:9])=[CH:18][CH:17]=3)=[CH:28][CH:27]=2)[C@H:22]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][N:35]=2)[CH2:23][C@@H:24]1[CH3:32])(=[O:31])[CH3:30]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67207670HCID 67207670, compound

Product 1

HCID 68161610HCID 68161610, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of phenylmethyl[(4-{(2S,4R)-1-acetyl-4-[(5-fluoro-2-pyridinyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}phenyl)methyl]methylcarbamate (for a preparation see intermediate 79) (55 mg, 0.100 mmol) and palladium (10% w/w on charcoal, 50% wet, 6.35 mg, 0.060 mmol) in ethanol (9 mL) was stirred under hydrogen (1 bar) at room temperature for 17 h then filtered through celite. The insoluble material was rinsed with ethanol (20 mL) and the combined filtrate and washings were concentrated in vacuo. Purification of the residue with MDAP (modifier: ammonium bicarbonate) gave a white solid which was dissolved in MeOH (0.4 mL), then treated with HCl (1.25M in MeOH, 38.3 μL, 0.0478 mmol). The resulting mixture was concentrated in vacuo to give (2S,4R)-1-acetyl-N-(5-fluoro-2-pyridinyl)-2-methyl-6-{4-[(methylamino)methyl]phenyl}-1,2,3,4-tetrahydro-4-quinolinamine hydrochloride (23 mg, 48%) as a pale yellow solid.

Workup

  1. filtrationthen filtered through celite
  2. washThe insoluble material was rinsed with ethanol (20 mL)
  3. concentrationthe combined filtrate and washings were concentrated in vacuo
  4. customPurification of the residue with MDAP (modifier: ammonium bicarbonate)
  5. customgave a white solid which
  6. concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-9c7f00ec98904cfb88830f294e3197f5
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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