Sodium Cyanate → 6-Ethyl-2-ureido-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

HRID 1483214

반응식

HRID 1483214 반응식
[NH2:1][C:2]1[S:12][C:5]2[CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:13]([NH2:15])=[O:14].[O-:16][C:17]#[N:18].[Na+]>C(O)(=O)C.O>[CH2:10]([N:7]1[CH2:8][CH2:9][C:4]2[C:3]([C:13]([NH2:15])=[O:14])=[C:2]([NH:1][C:17]([NH2:18])=[O:16])[S:12][C:5]=2[CH2:6]1)[CH3:11]

참가 물질

5

반응물 2

HCID 517096Sodium CyanateHCID 6144392-Amino-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

생성물 1

HCID 1182701246-Ethyl-2-ureido-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide수율 23.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

To a stirred mixture of compound F4 (451 mg, 2.00 mmol) in acetic acid (6 mL) at room temperature was added a solution of sodium cyanate (169 mg, 2.60 mmol) in water (2.5 mL) dropwise over 2 min. After addition, the reaction mixture was stirred for another 2 h and then concentrated under reduced pressure. The resulting residue was mixed with saturated aqueous sodium bicarbonate (50 mL) and extracted with methylene chloride (3×150 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with methanol/methylene chloride (15:85) to afford compound M1 as a yellow solid (125 mg, 23%): 1H NMR (300 MHz, DMSO-d6) δ 10.45 (s, 1H), 7.31 (bs, 1H), 6.77 (bs, 3H), 3.41 (s, 2H), 2.73 (d, J=4.8 Hz, 2H), 2.63 (d, J=4.8 Hz, 2H), 2.50-2.45 (m, 2H), 1.06 (t, J=7.0 Hz, 3H). MS (M+H) 269.

후처리

  1. additionAfter addition
  2. concentrationconcentrated under reduced pressure
  3. additionThe resulting residue was mixed with saturated aqueous sodium bicarbonate (50 mL)
  4. extractionextracted with methylene chloride (3×150 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by flash column chromatography on silica gel eluting with methanol/methylene chloride (15:85)

출처 및 근거

ORD 기록
ord-708cb3855ac8442382312e0e3e061088
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416141B2

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