Morpholine → HCID 59759168, compound

HRID 914370Notes

Reaction equation

C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[C:28]([O:32][C:33](=[O:60])[C:34]([S:37][C:38]1[S:39][CH:40]=[C:41]([CH2:43][CH2:44][N:45]([C:53]2[N:58]=[CH:57][C:56](Br)=[CH:55][N:54]=2)[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[N:42]=1)([CH3:36])[CH3:35])([CH3:31])([CH3:30])[CH3:29].[NH:61]1[CH2:66][CH2:65][O:64][CH2:63][CH2:62]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:28]([O:32][C:33](=[O:60])[C:34]([S:37][C:38]1[S:39][CH:40]=[C:41]([CH2:43][CH2:44][N:45]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:53]2[N:58]=[CH:57][C:56]([N:61]3[CH2:66][CH2:65][O:64][CH2:63][CH2:62]3)=[CH:55][N:54]=2)[N:42]=1)([CH3:36])[CH3:35])([CH3:31])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 110 °C

Procedure

Tris(dibenzylideneacetone)dipalladium (45 mg), 2-(di-tert-butylphosphino)biphenyl (29 mg) and sodium tert-butoxide (104 mg) were added to a 20 mL screw cap test tube substituted with nitrogen, and a solution of 2-[(4-{2-[(5-bromopyrimidin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (550 mg) synthesized in Example 442-1 and morpholine (129 mg) in toluene (2.0 mL) was added thereto. The test tube was capped, and stirred at 110° C. for 8 hr. After cooling to room temperature, the solution was directly packed and purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1 to 2:1) to give the title compound (300 mg) as a colorless oil.

Workup

customcap test tube
customThe test tube was capped
temperatureAfter cooling to room temperature
custompurified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1 to 2:1)

Sources & evidence

ORD record: ord-52347d7bdd9c4a0095233ff44d35805b
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026370B2

Reaction notes

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