Hydrochloric Acid → 3-[2-Amino-7-fluoro-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-6-ylsulfanyl]-benzaldehyde

HRID 658070Notes

Reaction equation

HRID 658070 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[CH:8]=[C:9]([S:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][C:23]=2[F:24])[N:20]=[C:19]([NH2:25])[C:18]([CH2:26][CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:17]3)[CH:10]=[CH:11][CH:12]=1.Cl.O>C(OCC)C>[NH2:25][C:19]1[C:18]([CH2:26][CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:17][C:16]2[C:21](=[CH:22][C:23]([F:24])=[C:14]([S:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[CH:2]=[O:1])[CH:15]=2)[N:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 687389956-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-7-fluoro-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-2-ylamine

Product 1

HCID 866342683-[2-Amino-7-fluoro-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-6-ylsulfanyl]-benzaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a μwave tube, 6-(3-[1,3]dioxan-2-yl-phenylsulfanyl)-7-fluoro-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-2-ylamine (45 mg, 0.1 mmol) was placed with HCl (conc.) (0.5 mL), H2O (0.5 mL) and diethyl ether (0.2 mL) were reacted via μwave @ 300W, 130° C. for 12 min. The resulting mixture was worked up by removal of solvent to yield a residue, which was purified by silica column chromatography (50% EtOAc/heptanes) to yield a solid.

Workup

  1. customThe resulting mixture was worked up by removal of solvent
  2. customto yield a residue, which
  3. customwas purified by silica column chromatography (50% EtOAc/heptanes)
  4. customto yield a solid

Sources & evidence

ORD record
ord-68320a40bd8d4c42b5ca975da5033588
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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