4-Methylmorpholine → HCID 67090705, compound

HRID 2075463Notes

Reaction equation

HRID 2075463 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.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH3:56][O:57][CH2:58][CH2:59][O:60][CH2:61][C:62](O)=[O:63]>>[CH3:56][O:57][CH2:58][CH2:59][O:60][CH2:61][C:62]([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:63]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 27642(2-Methoxyethoxy)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11427553(4-((1E)-2-(1H-Indazol-3-yl)ethenyl)phenyl)-1-piperazinylmethanone

Product 1

HCID 67090705HCID 67090705, compoundYield 4.1%

Procedure

The crude product obtain using Compound 18 (200 mg, 0.602 mmol), N-methylmorpholine (0.132 mL, 1.20 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (161 mg, 0.842 mmol), 1-hydroxybenzotriazole monohydrate (106 mg, 0.783 mmol) and 2-methoxyethoxyacetic acid (0.0674 mL, 0.722 mmol) in a similar manner to Example 5, was purified by silica gel column chromatography (chloroform/methanol=80/20) to obtain Compound 127 (0.011 g, 4%).

Workup

  1. customwas purified by silica gel column chromatography (chloroform/methanol=80/20)

Sources & evidence

ORD record
ord-409a827a57a1464e9a2e4ea6a2f9e3d8
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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