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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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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
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HRID 929248 반응식
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
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참가 물질

7

반응물 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-ol2회HCID 178514179HCID 178514179, 화합물

생성물 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

시약·촉매·용매 3

HCID 12976736Bis(ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane);iron(2+)촉매
HCID 6228Dimethylformamide용매
HCID 31374Dimethylacetamide용매2회

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-261154eec9234c74b31c62350ace5d3f
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09290517B2

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