Acetic Anhydride → N-[[2-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-5-(2,6-dimethyl-4-pyridinyl)-4-thiazolyl]methyl]-acetamide

HRID 473982ノート

反応式

HRID 473982 の反応式
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[S:10][C:11]([C:16]3[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([CH3:23])[CH:17]=3)=[C:12](NC)[N:13]=2)[CH2:3]1.[CH2:24]([N:26]([CH2:29]C)CC)[CH3:25].C(OC(=O)C)(=[O:33])C>ClCCl>[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[S:10][C:11]([C:16]3[CH:17]=[C:18]([CH3:23])[N:19]=[C:20]([CH3:22])[CH:21]=3)=[C:12]([CH2:29][NH:26][C:24](=[O:33])[CH3:25])[N:13]=2)[CH2:5]1

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67216071[2-(cis-2,6-Dimethyl-morpholin-4-yl)-5-(2,6-dimethyl-pyridin-4-yl)-thiazol-4-yl]-methylamine

生成物 1

HCID 53237123N-[[2-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-5-(2,6-dimethyl-4-pyridinyl)-4-thiazolyl]methyl]-acetamide収率 59.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of Intermediate 5 (150 mg, 0.45 mmol) and triethylamine (0.063 mL, 0.54 mmol) was stirred in dichloromethane (6 mL) at room temperature. Acetic acid anhydride (0.051 mL, 0.54 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was washed with a potassium carbonate solution. The organic layer was dried on MgSO4, filtered, and evaporated. The residue was purified by preparative HPLC (RP Shandon Hyperprep C18 BDS—8 μm, 250 g, 5 cm; mobile phase (0.25% NH4HCO3 solution in water, MeOH+CH3CN)), yielding 100 mg (59%) of Compound 60.

後処理

  1. washThe reaction mixture was washed with a potassium carbonate solution
  2. customThe organic layer was dried on MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by preparative HPLC (RP Shandon Hyperprep C18 BDS—8 μm, 250 g, 5 cm; mobile phase (0.25% NH4HCO3 solution in water, MeOH+CH3CN))

出典と根拠

ORDレコード
ord-4435f6b8aee34d05a7423ccff5df4417
出典データセット
uspto-grants-2014_01
特許番号
US08637510B2

反応ノート

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