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 1710991ノート

反応式

HRID 1710991 の反応式
[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

参加物

3

反応物 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

生成物 1

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

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e5a5e5aa84484ac683defa4aac671b64
出典データセット
uspto-grants-2010_09
特許番号
US07790729B2

反応ノート

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