4-Methylmorpholine → (E)-4-{4-[2-(1H-indazol-3-yl)vinyl]benzoyl}-1-(2-methoxyethyl)piperazin-2-one hydrochloride

HRID 2378749Notes

Reaction equation

HRID 2378749 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:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)=[N:2]1.CN1CCOCC1.[ClH:28].C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH3:51][O:52][CH2:53][CH2:54][N:55]1[CH2:60][CH2:59][NH:58][CH2:57][C:56]1=[O:61].C(OCC)(=O)C.Cl>>[ClH:28].[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:58]3[CH2:59][CH2:60][N:55]([CH2:54][CH2:53][O:52][CH3:51])[C:56](=[O:61])[CH2:57]3)=[O:18])=[CH:19][CH:20]=2)=[N:2]1

Participants

7

Reactant 6

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11437002(E)-4-(2-(1H-indazol-3-yl)vinyl)benzoic acidHCID 187839041-(2-Methoxyethyl)piperazin-2-oneHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 67090692(E)-4-{4-[2-(1H-indazol-3-yl)vinyl]benzoyl}-1-(2-methoxyethyl)piperazin-2-one hydrochlorideYield 12%

Procedure

The crude product obtained using (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid (50.0 mg, 0.189 mmol) obtained in Step 6 of Example 1, N-methylmorpholine (0.0415 mL, 0.378 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (50.7 mg, 0.265 mmol), 1-hydroxybenzotriazole monohydrate (33.2 mg, 0.246 mmol) and 1-(2-methoxyethyl)piperazin-2-one (44.8 mg, 0.284 mmol) in a similar manner to Step 7 of Example 1, was treated with hydrogen chloride-ethyl acetate solution (4 mol/L, 0.236 mL) to obtain Compound 134 (10.0 mg, 12%).

Sources & evidence

ORD record
ord-499efd8574c946d286c37d0dd35ae389
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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