Morpholine → HCID 90408081, compound

HRID 594079Notes

Reaction equation

HRID 594079 reaction equation
C(N(CC)CC)C.F[C:9]1[CH:14]=[C:13]([C:15]2[CH:16]=[C:17]([NH:22][C:23](=[O:34])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[CH:18]=[CH:19][C:20]=2[CH3:21])[CH:12]=[C:11]([F:35])[N:10]=1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>CO>[F:35][C:11]1[CH:12]=[C:13]([C:15]2[CH:16]=[C:17]([NH:22][C:23](=[O:34])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[CH:18]=[CH:19][C:20]=2[CH3:21])[CH:14]=[C:9]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[N:10]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 90410100HCID 90410100, compound

Product 1

HCID 90408081HCID 90408081, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of triethylamine (3.0 equiv.) and N-(3-(2,6-difluoropyridin-4-yl)-4-methylphenyl)-3-(trifluoromethyl)benzamide (1.0 equiv.) at RT in MeOH (0.12 M) was added morpholine (2.0 equiv) in one portion, the resulting mixture was then heated at 55° C. for 8 hours. LCMS analysis indicated 90% conversion to the desired product (M+H=460.1, Rt=0.43 min/non-polar). Water was then added, and the mixture was extracted with ethyl acetate, and the combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated to yield N-(3-(2-fluoro-6-morpholinopyridin-4-yl)-4-methylphenyl)-3-(trifluoromethyl)benzamide as a light brown solid (>100%). LCMS (m/z) (M+H)=460.1, Rt=0.43 min/non-polar.

Sources & evidence

ORD record
ord-d57729cfbd1d45359bcbb724f9c8f5d1
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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