4-Methylmorpholine → HCID 25095246, compound

HRID 2378747Notes

Reaction equation

HRID 2378747 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([NH:33][C:34]([CH3:39])([CH3:38])[C:35](O)=[O:36])=O)(C)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1.Cl.CO>CO>[NH2:33][C:34]([CH3:39])([CH3:38])[C:35]([N:21]1[CH2:22][CH2:23][N:18]([C:16](=[O:17])[C:15]2[CH:14]=[CH:13][C:12](/[CH:11]=[CH:10]/[C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][N:2]=3)=[CH:25][CH:24]=2)[CH2:19][CH2:20]1)=[O:36]

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 27960291-Hydroxybenzotriazole hydrateHCID 11427553(4-((1E)-2-(1H-Indazol-3-yl)ethenyl)phenyl)-1-piperazinylmethanoneHCID 21893726Hydrochloride methanol

Product 1

HCID 25095246HCID 25095246, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The product obtained using Compound 18 (300 mg, 0.90 mmol), 2-(tert-butoxycarbonyl)amino-2-methylpropionic acid (153 mg, 0.75 mmol), 1-hydroxybenzotriazole monohydrate (132 mg, 0.98 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (202 mg, 1.05 mmol) and N-methylmorpholine (0.16 mL, 1.50 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 131 (0.10 mg, 23%).

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-5b59b9fb9c8a46308c125dd4f42c70dd
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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