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Morpholine → HCID 10240432, compound

HRID 2237085
Notes
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Reaction equation

HRID 2237085 reaction equation
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[CH:28]([N:41]1[C:49]2[C:44](=[CH:45][C:46](Cl)=[CH:47][CH:48]=2)[C:43]([CH2:51][CH2:52][O:53][C:54]2[CH:62]=[CH:61][C:57]([C:58]([OH:60])=[O:59])=[CH:56][CH:55]=2)=[C:42]1[CH2:63][CH2:64][NH:65][S:66]([CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)(=[O:68])=[O:67])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[NH:76]1[CH2:81][CH2:80][O:79][CH2:78][CH2:77]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].C1(C)C=CC=CC=1>[CH:28]([N:41]1[C:49]2[C:44](=[CH:45][C:46]([N:76]3[CH2:81][CH2:80][O:79][CH2:78][CH2:77]3)=[CH:47][CH:48]=2)[C:43]([CH2:51][CH2:52][O:53][C:54]2[CH:62]=[CH:61][C:57]([C:58]([OH:60])=[O:59])=[CH:56][CH:55]=2)=[C:42]1[CH2:63][CH2:64][NH:65][S:66]([CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)(=[O:68])=[O:67])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8083MorpholineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 9874688HCID 9874688, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 10240432HCID 10240432, compoundYield 7.8%

Reagents, catalysts & solvents 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 1140TolueneSolvent

Procedure

Step 1—A flask was charged with tris(dibenzylideneacetone)dipalladium(0) (0.01 eq.), 2-(di-t-butylphosphino)biphenyl (0.04 eq.), sodium t-butoxide (2.4 eq.) and the acid from Example 1 step 8 (1.0 eq.). 1.5 ml toluene (1.0 M) was added to the flask followed by morpholine (1.2 eq.) The reaction was heated to reflux for five hours. The reaction mixture was partitioned between 5% hydrochloric acid and dietheyl ether. The organic layer was washed with distilled water, followed by brine, dried over sodium sulfate and concentrated. The product was purified by preparatory LC-MS to afford 7.8% of the desired product. HRMS calc for [C43H43N3O6S+H] 730.2945 found 730.2945.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for five hours
  3. customThe reaction mixture was partitioned between 5% hydrochloric acid and dietheyl ether
  4. washThe organic layer was washed with distilled water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified by preparatory LC-MS

Sources & evidence

ORD record
ord-0a2a5e67aa66415aad46f65e55175e01
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07713964B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes