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Methyl 3-mercaptopropionate → Ethyl 3-(5-(benzyloxy)-6-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)propanoate

HRID 1426161
ノート
印刷プレビュー

反応式

HRID 1426161 の反応式
[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][C:19]3[C:24]([N:25]=2)=[CH:23][CH:22]=[CH:21][N:20]=3)=[N:11][CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].[CH2:33](N(C(C)C)C(C)C)C.[Cl-].[NH4+]>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.ClCCl.O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([S:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:12]=[N:11][C:10]=1[NH:16][C:17]1[S:18][C:19]2[C:24]([N:25]=1)=[CH:23][CH:22]=[CH:21][N:20]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 18050Methyl 3-mercaptopropionateHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 16661301N-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine

生成物 1

HCID 86639698Ethyl 3-(5-(benzyloxy)-6-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)propanoate収率 110.7%

試薬・触媒・溶媒 5

HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

A 500 mL round-bottomed flask was charged with N-(3-(benzyloxy)-5-bromopyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine (2.00 g, 4.839 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.1400 g, 0.2420 mmol), Pd2dba3 (0.1108 g, 0.1210 mmol), methyl 3-mercaptopropanoate (0.5628 ml, 5.081 mmol), N-ethyl-N-isopropylpropan-2-amine (1.686 ml, 9.678 mmol), and dioxane (125 mL). The reaction mixture was heated at 95° C. under nitrogen for three hours. Saturated ammonium chloride and dichloromethane were added. The reaction mixture was filtered and the solids were washed with water to the title compound (2.425 g, 110.7% yield) containing a small amount of diisopropylethylamine impurity. 1H NMR (DMSO-d6) δ 10.89 (s, 1H), 8.36 (d, 1H), 7.96 (d, 1H), 7.95 (s, 1H), 7.60 (m, 3H), 7.42 (m, 3H), 7.35 (m, 1H), 5.34 (s, 2H), 3.59 (s, 3H), 3.12 (t, 2H), 2.54 (t, 2H). Mass spectrum (apci) m/z=453.1 (M+H).

後処理

  1. filtrationThe reaction mixture was filtered

出典と根拠

ORDレコード
ord-46a4db084f984238ba13b8b3eb19eb68
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933077B2

反応ノート

読み込み中…

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