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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
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HRID 1426161 반응식
[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
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참가 물질

10

반응물 4

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

생성물 1

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

시약·촉매·용매 5

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 962Water용매
HCID 6344Dichloromethane용매
HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

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).

후처리

  1. filtrationThe reaction mixture was filtered

출처 및 근거

ORD 기록
ord-46a4db084f984238ba13b8b3eb19eb68
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08933077B2

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