L-Leucine → (2S)-N-[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]-4-methylpentanamide hydrochloride

HRID 1008508

Reaktionsgleichung

Reaktionsgleichung von HRID 1008508
Cl.NC1C2C(=CC(CC(NC(=O)CNS(C3C(C)=C(C)C4OC(C)(C)CCC=4C=3C)(=O)=O)C(=O)N3CCCCC3)=CC=2)C=CN=1.[NH2:46][C:47]1[C:56]2[C:51](=[CH:52][C:53]([CH2:57][CH:58]([NH:67][C:68](=[O:74])OC(C)(C)C)[C:59](=[O:66])[N:60]3[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]3)=[CH:54][CH:55]=2)[CH:50]=[CH:49][N:48]=1.[CH3:75][O:76][C:77]1[CH:82]=[C:81]([CH3:83])[C:80]([S:84]([NH:87][C@@H:88]([CH2:92][CH:93]([CH3:95])[CH3:94])C(O)=O)(=[O:86])=[O:85])=[C:79]([CH3:96])[C:78]=1[CH3:97].N[C@H](C(O)=O)CC(C)C.COC1C=C(C)C(S([Cl:119])(=O)=O)=C(C)C=1C>>[ClH:119].[NH2:46][C:47]1[C:56]2[C:51](=[CH:52][C:53]([CH2:57][CH:58]([NH:67][C:68](=[O:74])[C@@H:88]([NH:87][S:84]([C:80]3[C:81]([CH3:83])=[CH:82][C:77]([O:76][CH3:75])=[C:78]([CH3:97])[C:79]=3[CH3:96])(=[O:86])=[O:85])[CH2:92][CH:93]([CH3:95])[CH3:94])[C:59](=[O:66])[N:60]3[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]3)=[CH:54][CH:55]=2)[CH:50]=[CH:49][N:48]=1

Komponenten

6

Edukt 5

HCID 6106L-LeucineHCID 5627874-Methoxy-2,3,6-trimethylbenzenesulfonyl chlorideHCID 226656071,1-Dimethylethyl 1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl-carbamateHCID 22665631HCID 22665631, VerbindungHCID 57069956(2S)-2-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]-4-methylpentanoic acid

Produkt 1

HCID 86588688(2S)-N-[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]-4-methylpentanamide hydrochloride

Versuchsvorschrift

The procedure described for 5c was used. Deprotection of 75 mg of 5a and coupling with 72 mg of (2S)-2-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]-4-methylpentanoic acid (prepared from L-leucine and 4-methoxy-2,3,6-trimethylphenylsulfonylchloride using the procedure described for 5b) yielded after purification the title compound (65 mg) as a mixture of diastereomers (1:1). 1H-NMR 400 MHz (CD3OD) δ: 0.50 and 0.68 (3H, 2× d, J=7 Hz), 0.61 and 0.79 (3H, 2× d, J=7 Hz), 0.97-1.65 (9H, m), 2.13 (3H, s), 2.54 and 2.56 (3H, 2× s), 2.61 and 2.62 (3H, 2× s), 2.76-3.68 (7H, m), 3.78 and 3.84 (3H, 2× s), 4.98-5.02 and 5.18-5.22 (1H, 2× m), 6.71 (1H, s), 7.16-7.19 (1H, m), 7.53-7.78 (4H, m), 8.29-8.34 (1H, m).

Aufarbeitung

  1. customyielded
  2. customafter purification the title compound (65 mg)
  3. additionas a mixture of diastereomers (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-50e0516a672b4859a0c12d39873f6b8e
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06797710B2

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