Nitrogen → Ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-8-yl)pyridine-2-carboxylate

HRID 1948047노트

반응식

HRID 1948047 반응식
[NH2:1][C:2]1[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:4][C:5]([C:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH:9]=2)=[CH:6][CH:7]=1.N#N>CCO.[Pd]>[NH2:1][C:2]1[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 947NitrogenHCID 67255067Ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine-2-carboxylate2회

생성물 1

HCID 67253957Ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-8-yl)pyridine-2-carboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

10% Pd/C (345 mg, 0.0812 mmol) was added to a solution of ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine-2-carboxylate (Compound 232F, 247 mg, 0.812 mmol) in EtOH (5.0 mL). The flask containing this mixture was subjected to 3 cycles of evacuation and N2 purging. After the 4th evacuation the flask was purged with H2 and allowed to stir for 24 hours. The reaction mixture was filtered through celite, the filter cake was washed with MeOH and DCM. The combined filtrate was concentrated to 228 mg of a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 1.30 (t, J=7.07 Hz, 3H), 1.59 (dd, J=12.51, 5.43 Hz, 2H), 1.63-1.70 (m, 2H), 1.70-1.79 (m, 4H), 2.59 (tt, J=11.15, 3.51 Hz, 1H), 3.87 (s, 4H), 4.28 (q, J=7.07 Hz, 2H), 6.50 (s, 2H), 7.17 (s, 2H). MS (ES+): m/z=306.91 (100) [M+1]. HPLC: tR=3.19 min (ZQ3, polar—5 min).

후처리

  1. additionThe flask containing this mixture
  2. customAfter the 4th evacuation the flask was purged with H2
  3. filtrationThe reaction mixture was filtered through celite
  4. washthe filter cake was washed with MeOH and DCM
  5. concentrationThe combined filtrate was concentrated to 228 mg of a yellow solid
  6. custom5 min

출처 및 근거

ORD 기록
ord-37364a5fbf10494286d195b5974ea396
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399433B2

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