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Sulfuric Acid → 5-([1,1'-biphenyl]-4-yl)-2-(((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl)oxy)-1H-imidazo[4,5-b]pyridine-6-carbonitrile

HRID 929248
ノート
印刷プレビュー

反応式

HRID 929248 の反応式
S(=O)(=O)(O)O.[C:6]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]3[N:18]=[C:19]([O:29][C@H:30]4[C@H:34]5[O:35][CH2:36][C@@H:37]([OH:38])[C@H:33]5[O:32][CH2:31]4)[N:20](COCC[Si](C)(C)C)[C:15]3=[CH:14][C:13]=2Cl)=[CH:8][CH:7]=1.[C:46]([Zn]C#N)#[N:47]>CC(N(C)C)=O.CN(C=O)C.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[C:6]1([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:7]=[CH:8][C:9]([C:12]2[N:17]=[C:16]3[N:18]=[C:19]([O:29][C@@H:30]4[CH2:31][O:32][C@@H:33]5[C@H:37]([OH:38])[CH2:36][O:35][C@H:34]45)[NH:20][C:15]3=[CH:14][C:13]=2[C:46]#[N:47])=[CH:10][CH:11]=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

7

反応物 3

HCID 1118Sulfuric AcidHCID 89558893(3R,3aR,6R,6aR)-6-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol2 回HCID 178514179HCID 178514179、化合物

生成物 1

HCID 900674605-([1,1'-biphenyl]-4-yl)-2-(((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl)oxy)-1H-imidazo[4,5-b]pyridine-6-carbonitrile

試薬・触媒・溶媒 3

HCID 12976736Bis(ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane);iron(2+)触媒
HCID 6228Dimethylformamide溶媒
HCID 31374Dimethylacetamide溶媒2 回

反応条件

温度
80 °C

実験手順

A mixture of PdOAc2 (15.48 mg, 0.069 mmol) and 1,1′-bis(di-tert-butylphoshino)ferrocene (32.7 mg, 0.069 mmol) in DMAc (0.25 ml) was treated with sulfuric acid (6.76 mg, 0.069 mmol) and stirred at 80° C. for 30 min. Then a solution of (3R,3aR,6R,6aR)-6-((5-([1,1′-biphenyl]-4-yl)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (Intermediate 8, 40 mg, 0.069 mmol) and dicyanozinc (9.71 mg, 0.083 mmol) in DMAc (0.25 ml) was added to the reaction and the reaction was heated to 120 degrees for 16 h. The residue was diluted with 0.7 ml DMF, filtered and purified by mass directed reverse phase column chromatography eluting with acetonitrile/water+0.1% TFA to give the title compound. LC-MS: calculated for C25H20N4O4, 440.15, observed m/e: 441.15 (M+H)+ (RT 0.58/2.00 min).

後処理

  1. temperaturethe reaction was heated to 120 degrees for 16 h
  2. filtrationfiltered
  3. custompurified by mass
  4. washeluting with acetonitrile/water+0.1% TFA

出典と根拠

ORDレコード
ord-261154eec9234c74b31c62350ace5d3f
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09290517B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート