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Water → 6,6-Dimethyl-2-[6-(2-methoxy-6-methylpyridin-3-yl)-2,3-dihydro-4h-1,4-benzoxazin-4-yl]-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

HRID 885979
ノート
印刷プレビュー

反応式

HRID 885979 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[CH2:14]C(C)(C)N[C:17](=O)[C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:30][O:31][C:32]1[C:37](B(O)O)=[CH:36][CH:35]=[C:34]([CH3:41])[N:33]=1.[OH2:42]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:5][C:6]1([CH3:23])[NH:7][C:14](=[O:42])[C:13]2[S:12][C:11]([N:7]3[C:6]4[CH:23]=[C:2]([C:37]5[C:32]([O:31][CH3:30])=[N:33][C:34]([CH3:41])=[CH:35][CH:36]=5)[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)=[N:19][C:18]=2[CH2:17]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27631212-Methoxy-6-methylpyridine-3-boronic acidHCID 685972362-(6-Bromo-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,6-dimethyl-6,7-dihydro-[1,3]thiazolo[5,4-d]pyridin-4(5h)-one

生成物 1

HCID 671874466,6-Dimethyl-2-[6-(2-methoxy-6-methylpyridin-3-yl)-2,3-dihydro-4h-1,4-benzoxazin-4-yl]-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one
収率 25%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
120 °C

実験手順

To a suspension of Example 39 (100 mg, 0.254 mmol) in THF (3 mL) and water (1 mL) was added tetra-n-butylammonium bromide (164 mg, 0.509 mmol), sodium carbonate (54 mg, 0.509 mmol), 2-methoxy-6-methylpyridine-3-boronic acid (85 mg, 0.509 mmol) and tetrakis(triphenylphosphine)palladium(0) (catalytic amount). The reaction was heated at 120° C. under microwave irradiation for 20 minutes. The resulting mixture was partitioned between DCM (50 mL) and water (50 mL); the organic fraction was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by preparative HPLC (Method 6) to yield the title compound (28 mg, 25%) as a beige solid. δH (CDCl3) 8.06 (1H, d, J 1.9 Hz), 7.50 (1H, d, J 7.3 Hz), 7.26 (1H, dd, J 8.5 and 2.1 Hz), 6.99 (1H, d, J 8.5 Hz), 6.81 (1H, d, J 7.5 Hz), 5.22 (1H, br. s), 4.39-4.31 (2H, m), 4.26-4.19 (2H, m), 4.00 (3H, s), 2.87 (2H, s), 2.49 (3H, s), 1.39 (6H, s). LCMS (ES+) 437.0 (M+H)+, RT 3.99 minutes (Method 1).

後処理

  1. customThe resulting mixture was partitioned between DCM (50 mL) and water (50 mL)
  2. washthe organic fraction was washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (Method 6)

出典と根拠

ORDレコード
ord-b1452365d4614765aafe695df75b6a00
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

読み込み中…

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