4-Methylmorpholine → HCID 69524860, compound

HRID 1241632Notes

Reaction equation

HRID 1241632 reaction equation
[C:1]([OH:11])(=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.ClN1C(OC)=NC(OC)=NC1.CN1CCOCC1.[CH2:30]([NH:34][C:35]([C@H:37]1[CH2:49][C:48]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[NH:41][C:40]=2[C@@H:39]([C:50]2[CH:58]=[CH:57][C:53]3[O:54][CH2:55][O:56][C:52]=3[CH:51]=2)[NH:38]1)=[O:36])[CH2:31][CH2:32][CH3:33]>O1CCCC1>[CH2:30]([NH:34][C:35]([C@H:37]1[CH2:49][C:48]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[NH:41][C:40]=2[C@@H:39]([C:50]2[CH:58]=[CH:57][C:53]3[O:54][CH2:55][O:56][C:52]=3[CH:51]=2)[N:38]1[C:1](=[O:11])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:36])[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 444539Cinnamic AcidHCID 21936586HCID 21936586, compoundHCID 58714355HCID 58714355, compound

Product 1

HCID 69524860HCID 69524860, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of trans-cinnamic acid (376 mg. 2.5 mmol), 2-chloro-3,5-dimethoxy-2,4,6-triazine (500 mg, 2.8 mmol), N-methylmorpholine (0.32 mL, 2.9 mmol), and tetrahydrofuran (20 mL) was stirred without cooling for 1.5 hours. Compound (XI) (1.0 g, 2.5 mmol) was added, then the reaction was stirred for an additional 18 hours. The solvent was evaporated, and the residue was dissolved in ethyl acetate, washed once with 1N hydrochloric acid, once with saturated sodium bicarbonate solution, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 30% ethyl acetate: 70% hexanes) of the residue provided 800 mg (61%) of Example 11 as a solid: mp 114–117° C.

Workup

  1. temperaturewithout cooling for 1.5 hours
  2. stirringthe reaction was stirred for an additional 18 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed once with 1N hydrochloric acid, once with saturated sodium bicarbonate solution
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80bbb363d52c48818d06f4d2cfe83608
Source dataset
uspto-grants-2006_10
Patent number
US07115621B2

Reaction notes

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