4-Methylmorpholine → HCID 67090483, compound

HRID 2075446Notes

Reaction equation

HRID 2075446 reaction equation
[C:1]1([NH2:12])[C:6](F)=[C:5](F)[C:4](F)=[C:3](N)[C:2]=1F.[ClH:13].Cl.N1C2C(=CC=CC=2)C(/C=C/C2C=CC(C(N3CCNCC3)=O)=CC=2)=N1.C(OC(NCC(O)=O)=O)(C)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1.C(OC([NH:89][CH2:90][C:91]([N:93]1[CH2:98][CH2:97][N:96]([C:99](=[O:117])[C:100]2[CH:105]=[CH:104][C:103](/[CH:106]=[CH:107]/[C:108]3C4C(=CC=CC=4)N[N:109]=3)=[CH:102][CH:101]=2)[CH2:95][CH2:94]1)=[O:92])=O)(C)(C)C.Cl.CO>>[ClH:13].[NH2:89][CH2:90][C:91]([N:93]1[CH2:98][CH2:97][N:96]([C:99](=[O:117])[C:100]2[CH:105]=[CH:104][C:103](/[CH:106]=[CH:107]/[C:108]3[C:2]4[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=4)[NH:12][N:109]=3)=[CH:102][CH:101]=2)[CH2:95][CH2:94]1)=[O:92]

Participants

9

Reactant 8

HCID 79724-MethylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 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 methanolHCID 67090572HCID 67090572, compound

Product 1

HCID 67090483HCID 67090483, compoundYield 64%

Procedure

In a similar manner to Example 5, (E)-4-(tert-butoxycarbonylamino)acetyl-1-{4-[2-(1H-indazol-3-yl)vinyl]benzoyl}piperazine was obtained using dihydrochloride of Compound 18 (800 mg, 2.18 mmol), N-(tert-butoxycarbonyl)glycine (314 mg, 1.79 mmol), 1-hydroxybenzotriazole monohydrate (315 mg, 2.56 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (482 mg, 2.51 mmol) and N-methylmorpholine (0.80 mL, 7.28 mmol). In a similar manner to Example 18, (E)-4-(tert-butoxycarbonylamino)acetyl-1-{4-[2-(1H-indazol-3-yl)vinyl]benzoyl}piperazine was treated with 10% hydrogen chloride-methanol solution to obtain Compound 61 (448 mg, 64%).

Sources & evidence

ORD record
ord-ba2b404bcaad42b9830fbc5ad924b329
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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