HCID 66906974, 화합물 → Thieno[3,2-b]pyridin-2-ylamine hydrochloride

HRID 1691552노트

반응식

HRID 1691552 반응식
[ClH:1].Br[C:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[S:5][C:4]=1[NH2:12]>CO.[Pd]>[ClH:1].[S:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:3]=[C:4]1[NH2:12]

참가 물질

4

반응물 1

HCID 66906974HCID 66906974, 화합물

생성물 1

HCID 66907303Thieno[3,2-b]pyridin-2-ylamine hydrochloride수율 57%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of compound 145-H, (1.86 g, 6.16 mmol) and 10% Pd/C (0.49 g, 26.3% w/w) in methanol (75 mL) was catalytically hydrogenated on a Parr shaker at 25 psi. After 3 h, the catalyst was filtered, the reaction mixture recharged with 10% Pd/C (0.49 g, 26.3% w/w) and shaken an additional 16 h at 22 psi H2. The reaction was filtered, recharged with 10% Pd/C (0.20 g, 10.8% w/w), and shaken at 20 psi H2 for an additional 24 h. The reaction mixture was filtered, evaporated, and the free base isolated by washing with aqueous sodium bicarbonate. The resultant residue was purified by flash column chromatography (SiO2), eluting with 3% MeOH/CH2Cl2 to afford compound 146-A as a yellow solid (0.65 g, 57%). 1H-NMR (DMSO-d6): δ 6.4 (s, 1H), 7.1 (dd, 1H), 8.3 (2, 1H), 8.4 (s, 2H), 8.5 (d, 1H), 15.2 (br s, 1H); MS: m/z 151.1 (MH+).

후처리

  1. filtrationthe catalyst was filtered
  2. filtrationThe reaction was filtered
  3. stirringshaken at 20 psi H2 for an additional 24 h
  4. filtrationThe reaction mixture was filtered
  5. customevaporated
  6. customthe free base isolated
  7. washby washing with aqueous sodium bicarbonate
  8. customThe resultant residue was purified by flash column chromatography (SiO2)
  9. washeluting with 3% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-a08559d0b57c427ca69356fe59e82c7b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153682B2

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