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Potassium Phosphate, Tribasic → 6-(4-Hydroxyphenyl)-1-(2-morpholinoethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 388113
ノート
印刷プレビュー

反応式

HRID 388113 の反応式
Cl.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]3[N:15]([CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[C:16](=[O:18])[NH:17][C:12]3=[N:11][CH:10]=2)=[CH:5][CH:4]=1.BrC1N=C2N(CCN3CCOCC3)C(=O)NC2=NC=1.CNC(C1C=CC(B(O)O)=CC=1)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]3[N:15]([CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[C:16](=[O:18])[NH:17][C:12]3=[N:11][CH:10]=2)=[CH:7][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 27735264-(Methylcarbamoyl)benzeneboronic acidHCID 866263996-Bromo-1-(2-morpholinoethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-oneHCID 1358710156-(4-Hydroxyphenyl)-1-(2-morpholinoethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride

生成物 1

HCID 1358710166-(4-Hydroxyphenyl)-1-(2-morpholinoethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one
収率 16%

試薬・触媒・溶媒 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

6-(4-Hydroxyphenyl)-1-(2-morpholinoethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride. 6-Bromo-1-(2-morpholinoethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (300 mg, 0.95 mmol), [4-(N-methylaminocarbonyl)phenyl]boronic acid (205 mg, 1.15 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane (80 mg, 0.09 mmol) and potassium phosphate (805 mg, 3.8 mmol) in DMF (30 mL) and water (8 mL) were reacted according to General Procedure C. The product was purified by reverse-phase semi-preparatory HPLC (30-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). The desired fractions were concentrated, treated with 4N hydrochloric acid in diethylether (few drops) and sonicated. This procedure was repeated twice more to provide 6-(4-hydroxyphenyl)-1-(2-morpholinoethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (67 mg, 16%) as a colorless solid hydrochloride salt. 1H NMR (400 MHz, CD3OD-d6) δ 8.38 (s, 1H), 8.84 (d, J=8.4, 2H), 7.44 (s, 1H), 7.39 (d, J=8.4, 2H), 4.45 (t, J=5.6, 2H); 4.07 (d, J=12.4, 2H), 3.82 (d, J=12.4, 2H), 3.69-3.64 (m, 4H); MS (ESI) m/z 342.15 [M+1]+.

後処理

  1. customThe product was purified by reverse-phase semi-preparatory HPLC (30-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)
  2. concentrationThe desired fractions were concentrated
  3. additiontreated with 4N hydrochloric acid in diethylether (few drops)
  4. customsonicated

出典と根拠

ORDレコード
ord-d9989113d74b4b4e889544bcbba84419
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08372976B2

反応ノート

読み込み中…

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