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

HRID 468678ノート

反応式

HRID 468678 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eb325b68e0034beb8ab7f8f5312f9a69
出典データセット
uspto-grants-2014_01
特許番号
US08624040B2

反応ノート

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