2-Chloro-6-morpholin-4-yl-pyrimidine-4-carboxylic acid[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-amide → HCID 59553189, compound

HRID 1641268Notes

Reaction equation

HRID 1641268 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH:20][C:21]([C:23]3[CH:28]=[C:27]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[N:26]=[C:25](Cl)[N:24]=3)=[O:22])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C(OCC)(=O)C.C(N(CC)CC)C.[Pd]>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH:20][C:21]([C:23]3[CH:28]=[C:27]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[N:26]=[CH:25][N:24]=3)=[O:22])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 595532362-Chloro-6-morpholin-4-yl-pyrimidine-4-carboxylic acid[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-amide

Product 1

HCID 59553189HCID 59553189, compoundYield 24.9%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-chloro-6-morpholin-4-yl-pyrimidine-4-carboxylic acid[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-amide (95 mg) and 10% Pd/C (10 mg) in ethyl acetate (4 ml) is added a few drops of triethylamine. The mixture is then shaken at room temperature under hydrogen at 50 psi for 8 h. The solvent is then removed under reduced pressure and the residue purified by column chromatography on silica gel eluted with ethyl acetate: hexane (1:1) to 100% ethyl acetate to provide 6-morpholin-4-yl-pyrimidine-4-carboxylic acid[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-amide as a solid (22 mg). Mp: 50-51° C. 1H NMR (300 MHz, DMSO-d6) δ 10.62 (s, 1H), 8.70 (s, 1H), 8.22 (d, J=7.2 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.66 (d, J=8.1 Hz, 1H), 7.57 (m, 2H), 7.42 (s, 1H), 7.04 (d, J=8.1 Hz, 1H), 4.30 (t, J=5.7, 2H), 3.70 (m, 10H), 3.60 (t, J=4.5 Hz, 2H) 2.87 (t, J=5.7 Hz, 2H), 2.56 (brm, 4H). MS: 463 (M+1).

Workup

  1. customThe solvent is then removed under reduced pressure
  2. customthe residue purified by column chromatography on silica gel
  3. washeluted with ethyl acetate: hexane (1:1) to 100% ethyl acetate

Sources & evidence

ORD record
ord-557634bc2495481e8f1b3510f7aed13e
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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