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

HRID 473982노트

반응식

HRID 473982 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-4435f6b8aee34d05a7423ccff5df4417
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637510B2

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