4-Methylmorpholine → HCID 67090053, compound

HRID 2075472Notes

Reaction equation

HRID 2075472 reaction equation
[C:1]1([NH2:12])[C:6](F)=[C:5](F)[C:4](F)=[C:3](N)C=1F.[ClH:13].Cl.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](/[CH:24]=[CH:25]/[C:26]2[CH:39]=[CH:38][C:29]([C:30]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[O:31])=[CH:28][CH:27]=2)=[N:16]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CC[O:67][CH2:66]C1.Cl.CO>CO>[ClH:13].[ClH:13].[NH:12]1[CH2:3][CH2:4][CH:5]([C:66]([N:35]2[CH2:36][CH2:37][N:32]([C:30](=[O:31])[C:29]3[CH:28]=[CH:27][C:26](/[CH:25]=[CH:24]/[C:17]4[C:18]5[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=5)[NH:15][N:16]=4)=[CH:39][CH:38]=3)[CH2:33][CH2:34]2)=[O:67])[CH2:6][CH2:1]1

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11427553(4-((1E)-2-(1H-Indazol-3-yl)ethenyl)phenyl)-1-piperazinylmethanoneHCID 21893726Hydrochloride methanol

Product 1

HCID 67090053HCID 67090053, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The product obtained using dihydrochloride of Compound 18 (200 mg, 0.49 mmol), isonipocotic acid tert-butyl ester (122 mg, 0.49 mmol), 1-hydroxybenzotriazole monohydrate (86 mg, 0.64 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (132 mg, 0.69 mmol) and N-methylmorpholine (0.1 mL, 0.98 mmol) in a similar manner to Example 5, was dissolved in methanol (2.00 mL), and the solution was added with 4 mol/L hydrogen chloride-methanol solution (1.50 mL), followed by heating under reflux at 60° C. for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from acetone to obtain Compound 142 (0.09 mg, 41%).

Workup

  1. customThe product obtained
  2. temperatureby heating
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was crystallized from acetone

Sources & evidence

ORD record
ord-65f26a64949d495fb944f6db07158162
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

Loading…