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Triethylamine → 6,6-Dimethyl-2-{6-[(2-methylpyrimidin-4-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

HRID 885991
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HRID 885991 반응식
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][C:10]2[CH:11]=[CH:12][C:13]3[O:18][CH2:17][CH2:16][N:15]([C:19]4[S:20][C:21]5[C:22](=[O:30])[NH:23][C:24]([CH3:29])([CH3:28])[CH2:25][C:26]=5[N:27]=4)[C:14]=3[CH:31]=2)[CH:3]=1.C(N(CC)CC)C>CO.[Pd]>[CH3:28][C:24]1([CH3:29])[NH:23][C:22](=[O:30])[C:21]2[S:20][C:19]([N:15]3[C:14]4[CH:31]=[C:10]([O:9][C:4]5[CH:3]=[CH:2][N:7]=[C:6]([CH3:8])[N:5]=5)[CH:11]=[CH:12][C:13]=4[O:18][CH2:17][CH2:16]3)=[N:27][C:26]=2[CH2:25]1
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참가 물질

5

반응물 2

HCID 8471TriethylamineHCID 248558182-{6-[(6-Chloro-2-methylpyrimidin-4-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

생성물 1

HCID 248558536,6-Dimethyl-2-{6-[(2-methylpyrimidin-4-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one수율 65%

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 887
Methanol
용매

실험 절차

To a suspension of Example 394 (40 mg, 0.088 mmol) in MeOH (15 mL) was added triethylamine (0.040 mL, 0.263 mmol) and 5% Pd/C (10 mg, 25% wt). The reaction mixture was stirred under an atmosphere of hydrogen for 24 h, then the catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was partitioned between DCM (50 mL) and water (50 mL); the organic phase was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo to give the title compound (24 mg, 65%) as an off-white solid. δH (CDCl3) 8.45 (1H, d, J 5.8 Hz), 7.97 (1H, d, J 2.6 Hz), 6.98 (1H, d, J 8.9 Hz), 6.84 (1H, dd, J 8.9 and 2.6 Hz), 6.63 (1H, d, J 5.8 Hz), 5.58 (1H, s), 4.41-4.26 (2H, m), 4.16-4.05 (2H, m), 2.84 (2H, s), 2.62 (3H, s), 1.37 (6H, s). LCMS (ES+) 424.0 (M+H)+, RT 2.75 minutes (Method 1).

후처리

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between DCM (50 mL) and water (50 mL)
  4. washthe organic phase was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-611fe985321c41e9bbb16998a11a8984
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08242116B2

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