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tert-butyl 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)piperidine-1-carboxylate

HRID 1676363
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HRID 1676363 반응식
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:31])[CH:3]=1.[H][H]>[Pd].CO>[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([CH:16]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[CH2:18][CH2:17]4)[S:15][C:8]=23)=[C:4]([F:31])[CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 59684980tert-butyl 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67346565Tert-butyl 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)piperidine-1-carboxylate수율 98.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887
Methanol
용매

실험 절차

A round-bottomed flask was charged with tert-butyl 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl) -5,6-dihydropyridine-1(2H)-carboxylate (Example 149, Step A, 146.3 mg, 0.3314 mmol), palladium on carbon (117.7 mg, 0.099 mmol, 10%) and MeOH (10 mL). The air was exchanged with nitrogen three times and then was exchanged with hydrogen another three times. Then the reaction mixture was stirred under hydrogen at room temperature until the starting material had been consumed (2 hours). The mixture was filtered to remove the palladium on carbon and then the solvent was removed under reduced pressure to afford crude product. The crude product was purified by silica gel chromatography (dichloromethane/7 M NH3 in MeOH from 100/1 to 10/1, v/v) to afford product (144.5 mg, 98.3%). LRMS (APCI pos): >95% purity, 254 nm, m/e 444 (M+1). 1H NMR (400 MHz, CD3Cl) δ 8.41 (d, 1H), 7.27 (m, 1H), 7.02 (t, 1H), 6.54 (dd, 1H), 6.46 (m, 2H), 4.24 (m, 2H), 3.84 (br s, 2H), 3.07 (m, 1H), 2.88 (m, 2H), 2.09 (m, 2H), 1.74 (m, 2H), 1.49 (s, 9H).

후처리

  1. customhad been consumed (2 hours)
  2. filtrationThe mixture was filtered
  3. customto remove the palladium on carbon
  4. customthe solvent was removed under reduced pressure
  5. customto afford crude product
  6. customThe crude product was purified by silica gel chromatography (dichloromethane/7 M NH3 in MeOH from 100/1 to 10/1

출처 및 근거

ORD 기록
ord-c7f3938e67a3474590e92fd0d037114c
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08003662B2

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