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Sodium Hydroxide → HCID 11999035, 화합물

HRID 1364104
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HRID 1364104 반응식
[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=[O:17])[CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[S:9][C:5]=2[CH:4]([OH:17])[CH2:3]1
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참가 물질

5

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HCID 14798Sodium HydroxideHCID 6222625,5-dimethyl-2-morpholin-4-yl-5,6-dihydro-1,3-benzothiazol-7(4H)-oneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 11999035HCID 11999035, 화합물수율 52.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of Example 48 (0.13 g, 0.5 mmol) in THF (10 mL) at r.t. was added LiAlH4 (0.5 mL, 1M solution in THF, 0.5 mmol) dropwise. The reaction mixture was stirred at r.t. for 2 h and then poured into 10% NaOH solution (20 mL) and extracted with DCM (2×20 mL). The combined organic fractions were dried over MgSO4, filtered and the solvent removed by evaporation in vacuo. Purification by column chromatography gave the title compound (0.07 g, 52%) as a solid. δH (DMSO-d6) 5.23 (1H, d, J 6.5 Hz), 4.65 (1H, dt, J 8.1 and 6.7 Hz), 3.77-3.70 (4H, m), 3.39 (4H, m), 2.40-2.24 (2H, m), 1.84 (1H, dd, J 5.9 and 11.3 Hz), 1.48 (1H, dd, J 8.8 and 12.6 Hz), 1.09 (3H, s), 0.94 (3H, s). LCMS (ES+) 269.0 (M+H)+.

후처리

  1. extractionextracted with DCM (2×20 mL)
  2. dry with materialThe combined organic fractions were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed by evaporation in vacuo
  5. customPurification by column chromatography

출처 및 근거

ORD 기록
ord-a37019d45bfd4022a4723d1c80da9d9c
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07888344B2

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