4-Methylmorpholine → HCID 67089641, compound

HRID 2075461Notes

Reaction equation

HRID 2075461 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:25]=[CH:24][C:15]([C:16]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:17])=[CH:14][CH:13]=2)=[N:2]1.C(OC([N:33]1[CH2:37][CH2:36][C@H:35]([C:38](O)=[O:39])[CH2:34]1)=O)(C)(C)C.O.ON1C2C=CC=CC=2N=N1.[ClH:52].C(N=C=NCCCN(C)C)C.CN1CCOCC1.Cl.CO>CO>[ClH:52].[ClH:52].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:38]([C@H:35]4[CH2:36][CH2:37][NH:33][CH2:34]4)=[O:39])[CH2:20][CH2:19]3)=[O:17])=[CH:24][CH:25]=2)=[N:2]1

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 1512492(3S)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acidHCID 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 67089641HCID 67089641, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The product obtained using Compound 18 (300 mg, 0.90 mmol), (S)-pyrrolidin-1,3-dicarboxylic acid 1-tert-butyl ester (162 mg, 0.76 mmol), 1-hydroxybenzotriazole monohydrate (133 mg, 0.99 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (204 mg, 1.06 mmol) and N-methylmorpholine (0.17 mL, 1.52 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 124 (278 mg, 61%).

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-050bba7b5bff4df5adfed735fed363d3
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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