홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

(5-Cyano-1-benzothiophen-2-yl)boronic acid → HCID 90284814, 화합물

HRID 2173079
노트
인쇄 미리보기

반응식

HRID 2173079 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20](Cl)[C:19]3[C:23](=[O:33])[N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C:18]=3[C:17]=2[F:34])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:35]([C:37]1[CH:48]=[CH:47][C:40]2[S:41][C:42](B(O)O)=[CH:43][C:39]=2[CH:38]=1)#[N:36]>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O.C([O-])(O)=O.[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20]([C:42]3[S:41][C:40]4[CH:47]=[CH:48][C:37]([C:35]#[N:36])=[CH:38][C:39]=4[CH:43]=3)[C:19]3[C:23](=[O:33])[N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C:18]=3[C:17]=2[F:34])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 2

HCID 53398611(5-Cyano-1-benzothiophen-2-yl)boronic acidHCID 86654748tert-Butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-4-chloro-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

생성물 1

HCID 90284814HCID 90284814, 화합물

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매
HCID 8857
Ethyl Acetate
용매
HCID 10340Sodium Carbonate용매
HCID 312751,4-Dioxane용매
HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of tert-butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-4-chloro-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (100 mg, 0.200 mmol), 5-cyanobenzo[b]thiophen-2-ylboronic acid (40.5 mg, 0.200 mmol) and tetrakis(triphenylphosphine)palladium(0) (231 mg, 0.200 mmol) in dioxane and saturated aqueous Na2CO3 (3:5, 6 mL) was heated to 120° C. in a microwave for 30 minutes. The reaction mixture was diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was separated and the aqueous layer was washed with EtOAc (50 mL). The organic layers were combined, dried over Na2SO4, and the solvent was removed in vacuo to give the intermediate, tert-butyl 6-(((3R,4R)-3-((tert-butoxycarbonyl)amino)tetrahydro-2H-pyran-4-yl)amino)-4-(5-cyanobenzo[b]thiophen-2-yl)-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate. The intermediate was dispersed in TFA and DCM (1:1, 10 mL) and the mixture was stirred at room temperature for 60 minutes. The mixture was concentrated, reconstituted in MeOH and DCM (10.0 mL) and purified via preparative HPLC eluting with a gradient of 10-25% ACN (0.035% TFA) and H2O (0.05% TFA). The collected fractions were combined and diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was separated and the aqueous layer was washed with EtOAc (50 mL). The organic layers were combined, dried over Na2SO4, and the solvent was removed in vacuo to give the title compound (26 mg, 31%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.78 (dd, J=13.42, 4.15 Hz, 1H), 1.87-2.05 (m, 1H), 3.17-3.25 (m, 1H), 3.45-3.57 (m, 1H), 3.67 (d, J=10.25 Hz, 1H), 3.80 (br s, 1H), 3.91 (d, J=11.23 Hz, 1H), 4.26 (d, J=4.39 Hz, 1H), 4.43 (s, 2H), 7.00 (d, J=6.35 Hz, 1H), 7.72 (dd, J=8.30, 1.46 Hz, 1H), 8.20 (d, J=8.30 Hz, 1H), 8.47 (d, J=1.46 Hz, 1H), 8.61 (s, 1H), 9.50 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C21H18FN5O2S, 424. found, 424.

후처리

  1. customThe organic layer was separated
  2. washthe aqueous layer was washed with EtOAc (50 mL)
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-c2133e1f2c5b4b8a92b6baf4dce5b37d
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09056873B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트