Methanol → HCID 59553262, compound

HRID 1171359Notes

Reaction equation

HRID 1171359 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:31]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[CH3:38][OH:39]>CS(C)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:31]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([O:39][CH3:38])[N:20]=2)=[CH:10][CH:9]=1)=[O:6]

Participants

5

Reactant 2

HCID 887MethanolHCID 595530953-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide

Product 1

HCID 59553262HCID 59553262, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide (0.1 mmol) and methanol (1.0 ml) in DMSO (0.5 ml) is heated using a microwave source at 180° C. for 5 min. The resulting mixture is diluted with CH2Cl2 (5 ml), washed with water, dried over Na2SO4 and concentrated. Purification of the residue by column chromatography on silica gel (50% EtOAc in hexane) gives 3-fluoro-N-{4-[(2-methoxypyrimidin-4-yl)oxy]-1-naphthyl}-5-morpholin-4-ylbenzamide as a white solid (31 mg). Mp: 216-217° C.; 1H NMR (300 MHz, CDCl3) δ 3.25 (t, J=4.8 Hz, 4H), 3.84 (s, 3H), 3.87 (t, J=4.8 Hz, 4H), 6.53 (d, J=5.7 Hz, 1H), 6.77 (d, J=12 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H), 7.31-7.34 (m, 2H), 7.49-7.60 (m, 2H), 7.89-7.97 (m, 3H), 8.15 (s, 1H), 8.36 (d, J=5.7 Hz, 1H); MS 475 (M+1).

Workup

  1. temperatureis heated
  2. customat 180° C.
  3. customfor 5 min
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification of the residue by column chromatography on silica gel (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-7ab2fe3b45c84ec7b8f4544fb51d23bb
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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