4-Methylmorpholine → HCID 46081124, compound

HRID 2065538Notes

Reaction equation

HRID 2065538 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.Cl.[CH3:31][O:32][C:33]1[C:38]([CH3:39])=[CH:37][C:36]([CH:40]2[CH2:45][N:44]3[CH:46]=[C:47]([C:49]([OH:51])=O)[N:48]=[C:43]3[CH2:42][CH2:41]2)=[CH:35][C:34]=1[CH3:52].[C:53]1([CH:59]([N:66]2[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]2)[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>CN(C=O)C>[CH:59]([N:66]1[CH2:71][CH2:70][N:69]([C:49]([C:47]2[N:48]=[C:43]3[CH2:42][CH2:41][CH:40]([C:36]4[CH:37]=[C:38]([CH3:39])[C:33]([O:32][CH3:31])=[C:34]([CH3:52])[CH:35]=4)[CH2:45][N:44]3[CH:46]=2)=[O:51])[CH2:68][CH2:67]1)([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 70048BenzhydrylpiperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68907890HCID 68907890, compound

Product 1

HCID 46081124HCID 46081124, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TBTU (212 mg; 0.66 mmol) and N-methylmorpholine (181 μl; 167 mg; 1.65 mmol) were added to a solution of 6-(4-methoxy-3,5-dimethylphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid hydrochloride (165 mg; 0.49 mmol) in DMF (1 ml). The reaction mixture was stirred vigorously for 30 min at room temperature and then diphenylmethylpiperazine (166 mg; 0.7 mmol) was added. The reaction mixture was stirred for 4 h at room temperature and poured onto water. The precipitated solid was filtered. Yield: 232 mg (88%).

Workup

  1. stirringThe reaction mixture was stirred for 4 h at room temperature
  2. additionpoured onto water
  3. filtrationThe precipitated solid was filtered

Sources & evidence

ORD record
ord-f4b319a5f58c47259961d6adcc603663
Source dataset
uspto-grants-2012_10
Patent number
US08288424B2

Reaction notes

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