Morpholine → HCID 66661889, compound

HRID 2193474Notes

Reaction equation

HRID 2193474 reaction equation
C(OC([N:7]1[CH2:12][CH2:11][C:10]2[C:13]([C:27](=[O:29])[NH2:28])=[C:14]([NH:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[O:18])[S:15][C:9]=2[CH2:8]1)=O)C=C.N1CCOCC1>C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:17](=[O:18])[NH:16][C:14]2[S:15][C:9]3[CH2:8][NH:7][CH2:12][CH2:11][C:10]=3[C:13]=2[C:27]([NH2:28])=[O:29])=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 66661923HCID 66661923, compound

Product 1

HCID 66661889HCID 66661889, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Starting material 9 (750 mg, 1.7 mmol) was dissolved under Nitrogen atmosphere in 10 ml DCM in a 2 necked flask and a solution of morpholine (3 ml, 34.5 mmol) in 34.5 ml DCM was added. The solution was stirred for 5 Min. then a solution of Tetrakis(triphenylphosphin)-palladium(0) (199 mg, 0.2 mmol) in 17.2 ml DCM was added. After about 8 Min a brown suspension was formed. The reaction was stirred at ambient temperature for another 40 Min. The solvent was then reduced and product 5 was thereby isolated in two fractions: very pure as white crystals (246 mg, 0.7 mmol, 41%) and with 56% content in a brown solid (250 mg, 56% Gehalt an 5, 0.4 mmol), which contained side products as well but could be purified by prep. HPLC (Method 2). The pure product fractions were merged, the solvent reduced and the product lyophilized.

Workup

  1. customAfter about 8 Min a brown suspension was formed
  2. stirringThe reaction was stirred at ambient temperature for another 40 Min

Sources & evidence

ORD record
ord-9e1276794f414516b027d73c54c91171
Source dataset
uspto-grants-2012_12
Patent number
US08329907B2

Reaction notes

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