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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
ノート
印刷プレビュー

反応式

HRID 885991 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 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)-one収率 65%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 887
Methanol
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-611fe985321c41e9bbb16998a11a8984
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08242116B2

反応ノート

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