Hydrochloric Acid → N2-hydroxy-7,7-dimethyl-N5-[(1S)-1-phenylethyl]-6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxamide

HRID 468678노트

반응식

HRID 468678 반응식
[CH3:1][C:2]1([CH3:21])[CH2:7][NH:6][CH2:5][C:4]2[CH:8]=[C:9]([C:11]([NH:13][O:14]C3CCCCO3)=[O:12])[S:10][C:3]1=2.C(N(CC)CC)C.[C:29]1([C@@H:35]([N:37]=[C:38]=[O:39])[CH3:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl.O1CCOCC1>ClCCCl.O1CCCC1>[OH:14][NH:13][C:11]([C:9]1[S:10][C:3]2[C:2]([CH3:1])([CH3:21])[CH2:7][N:6]([C:38]([NH:37][C@H:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH3:36])=[O:39])[CH2:5][C:4]=2[CH:8]=1)=[O:12]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 2724173(S)-(-)-1-Phenylethyl isocyanateHCID 581576817,7-dimethyl-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide

생성물 1

HCID 58157558N2-hydroxy-7,7-dimethyl-N5-[(1S)-1-phenylethyl]-6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxamide수율 47.7%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 7,7-dimethyl-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide (31 mg, 0.1 mmol) and triethylamine (41.8 μL, 0.3 mmol) in 1,2-dichloroethane (1 mL) was added (S)-1-phenylethyl isocyanate (22.1 mg, 0.15 mmol). The reaction was stirred at room temperature overnight. The solution was evaporated to dryness and the residue obtained was redissolved in tetrahydrofuran (1 mL). 4.0 M of hydrochloric acid in 1,4-dioxane (1 mL, 4 mmol) was added and the reaction solution was stirred at room temperature for 2 hours. The solution was evaporated to dryness, redissolved in DMSO (1 mL) and purified on an Agilent 1100 LC/MSD instrument to afford the title compound (17.8 mg, 46%). LCMS (FA) ES+ 374; 1H NMR (400 MHz, MeOD) δ 7.35-7.24 (m, 5H), 7.20-7.15 (m, 1H), 5.01-4.91 (m, 1H), 4.50 (d, J=4.0 Hz, 2H), 3.50 (d, J=4.6 Hz, 2H), 1.47 (d, J=7.1 Hz, 3H), 1.30 (s, 6H).

후처리

  1. customThe solution was evaporated to dryness
  2. customthe residue obtained
  3. stirringthe reaction solution was stirred at room temperature for 2 hours
  4. customThe solution was evaporated to dryness
  5. dissolutionredissolved in DMSO (1 mL)
  6. custompurified on an Agilent 1100 LC/MSD instrument

출처 및 근거

ORD 기록
ord-eb325b68e0034beb8ab7f8f5312f9a69
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08624040B2

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