Methylamine → HCID 86716107, compound

HRID 627545Notes

Reaction equation

HRID 627545 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]3[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1.[CH3:33][NH2:34].[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>CCO.CN(C=O)C>[Cl:1][C:2]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([NH:34][CH3:33])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]3[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1.[C:37]([OH:39])([C:36]([F:41])([F:40])[F:35])=[O:38]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 6422Trifluoroacetic acidHCID 74222810HCID 74222810, compound

Product 1

HCID 86716107HCID 86716107, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (2,4-dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)pyridin-4-ylmethanol (28 mg, 0.0607 mmol, Example 16), 33% MeNH2 in EtOH (0.8 mL), and trifluoroacetic acid (0.050 mL, 0.653 mmol) was heated at 80° C. for 17 hours. After cooling to room temperature, the mixture was diluted with DMF and purified by reverse phase HPLC (water/acetonitrile/0.1% TFA) to give the title compound. 1H NMR (400 MHz, MeOH-d4) δ 9.08 (s, 1H), 8.74-8.83 (m, 2H), 8.49 (d, J=1.71 Hz, 1H), 7.98 (dt, J=1.93, 6.91 Hz, 3H), 7.86 (d, J=8.80 Hz, 1H), 7.47-7.55 (m, 3H), 7.35-7.46 (m, 2H), 7.25 (d, J=1.47 Hz, 1H), 3.69 (s, 3H), 2.58 (s, 3H); MS m/e 456.1 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. custompurified by reverse phase HPLC (water/acetonitrile/0.1% TFA)

Sources & evidence

ORD record
ord-609981c79dec42ce80a2a43b0c81ffcf
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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