L-Serine, methyl ester, hydrochloride (1:1) → methyl N-[(4-{3-tert-butyl-5-[({[4-(pyridin-4-yloxy)phenyl]amino}carbonyl)amino]-1H-pyrazol-1-yl}phenyl)acetyl]-L-serinate

HRID 221916

Reaktionsgleichung

Reaktionsgleichung von HRID 221916
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)=[O:12])[N:7]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][C:34](N3CC[C@H](O)C3)=[O:35])=[CH:29][CH:28]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:43][O:44][C:45](=[O:50])[C@H:46]([CH2:48][OH:49])[NH2:47]>>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:18][CH:19]=2)=[O:12])[N:7]([C:27]2[CH:28]=[CH:29][C:30]([CH2:33][C:34]([NH:47][C@H:46]([C:45]([O:44][CH3:43])=[O:50])[CH2:48][OH:49])=[O:35])=[CH:31][CH:32]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

3

Edukt 2

HCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 11592090N-[3-tert-butyl-1-(4-{2-[(3S)-3-hydroxypyrrolidin-1-yl]-2-oxoethyl}phenyl)-1H-pyrazol-5-yl]-N'-[4-(pyridin-4-yloxy)phenyl]urea

Produkt 1

HCID 11692791methyl N-[(4-{3-tert-butyl-5-[({[4-(pyridin-4-yloxy)phenyl]amino}carbonyl)amino]-1H-pyrazol-1-yl}phenyl)acetyl]-L-serinateAusbeute 62 %

Versuchsvorschrift

The title compound was prepared in the same manner as described for N-[3-tert-butyl-1-(4-{2-[(3S)-3-hydroxypyrrolidin-1-yl]-2-oxoethyl}phenyl)-1H-pyrazol-5-yl]-N′-[4-(pyridin-4-yloxy)phenyl]urea, replacing (S)-3-pyrrolidinol with L-serine methyl ester hydrochloride. The desired product was purified by MPLC (EtOAc/hexane/MeOH) and obtained as a solid (150 mg) in 62% yield. A sample of this material was purified further by HPLC and the TFA salt isolated from HPLC was neutralized to provide the title compound. 1H-NMR (DMSO-d6) δ 9.12 (s, 1H), 8.50 (d, J=7.9 Hz, 1H) 8.40 (m, 3H), 7.50-7.38 (m, 6H), 7.07 (d, J=8.7 Hz, 2H), 6.85 (m, 2H), 6.34 (s, 1H), 5.10 (t, J=5.4 Hz, 1H), 4.35 (m, 1H), 3.72 (m, 1H), 3.61 (m, 6H), 1.27 (s, 9H); MS LC-MS [M+H]+=587.2, RT=2.27 min.

Aufarbeitung

  1. customThe desired product was purified by MPLC (EtOAc/hexane/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-07d30cf2936a407ebb786bb3e71e0c49
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207166B2

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