1-(4-(2-(Dimethylcarbamoyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thiourea → N-(3-Fluoro-4-(6-(pyrrolidine-1-carbonyl)thieno[2,3-d]pyrimidin-4-yloxy)phenylcarbamothioyl)-2-phenylacetamide

HRID 1710991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710991
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[C:8]3[CH:15]=[C:14]([C:16]([N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[O:17])[S:13][C:9]=3[N:10]=[CH:11][N:12]=2)=[C:4]([F:25])[CH:3]=1.CN(C)C(C1SC2C(=NC=CC=2OC2C=CC(N[C:47]([NH:49][C:50](=[O:58])[CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)=[S:48])=CC=2F)C=1)=O>>[F:25][C:4]1[CH:3]=[C:2]([NH:1][C:47]([NH:49][C:50](=[O:58])[CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)=[S:48])[CH:24]=[CH:23][C:5]=1[O:6][C:7]1[C:8]2[CH:15]=[C:14]([C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[S:13][C:9]=2[N:10]=[CH:11][N:12]=1

Komponenten

3

Edukt 2

HCID 115407241-(4-(2-(Dimethylcarbamoyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thioureaHCID 59424640(4-(4-Amino-2-fluorophenoxy)thieno[2,3-d]pyrimidin-6-yl)(pyrrolidin-1-yl)methanone

Produkt 1

HCID 59424601N-(3-Fluoro-4-(6-(pyrrolidine-1-carbonyl)thieno[2,3-d]pyrimidin-4-yloxy)phenylcarbamothioyl)-2-phenylacetamideAusbeute 17 %

Versuchsvorschrift

Starting from the compound 210 and following the procedures described above for the synthesis of compound 8a (scheme 1, step 7, example 1), crude title compound 211 was obtained. It was purified by flash chromatography, eluents DCM and DCM-MeOH-Et3N (97.75:2:0.25) followed by trituration with a mixture of MeOH-EtOAc, to afford title compound 211 in 17% yield as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.43 (s, 1H), 11.80 (s, 1H), 8.70 (s, 1H), 8.06 (s, 1H), 7.93 (d, 1H, J=11.7/2.3 Hz), 7.53-7.47 (m, 2H), 7.34-7.26 (m, 5H), 3.90 (t, 2H, J=6.7 Hz), 3.83 (s, 2H), 3.55 (t, 2H, J=6.7 Hz), 1.99-1.85 (m, 4H). LRMS (M+1) 536.2 (100%).

Aufarbeitung

  1. customcrude title compound 211 was obtained
  2. customIt was purified by flash chromatography, eluents DCM and DCM-MeOH-Et3N (97.75:2:0.25)
  3. additionfollowed by trituration with a mixture of MeOH-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-e5a5e5aa84484ac683defa4aac671b64
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790729B2

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