Triethylamine → 3-[5-chloro-4-(3-methoxy-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-N-methoxy-4,N-dimethyl-benzamide

HRID 2172609노트

반응식

HRID 2172609 반응식
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:12](O)=[O:13])[C:5]([CH3:19])=[N:4][C:3]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1.[C:30](N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:43][N:44](C)[OH:45].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:12]([N:44]([O:45][CH3:30])[CH3:43])=[O:13])[C:5]([CH3:19])=[N:4][C:3]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 866862933-[5-chloro-4-(3-methoxy-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid

생성물 1

HCID 715826483-[5-chloro-4-(3-methoxy-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-N-methoxy-4,N-dimethyl-benzamide수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-[5-chloro-4-(3-methoxy-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid from step C (230 mg, 0.56 mmol) in tetrahydrofuran (2 mL) was added 1,1′-carbonyldiimidazole (135 mg, 0.83 mmol). After stirring at ambient temperature for three hours, N,N-dimethylhydroxylamine HCl (80 mg, 0.83 mmol) and triethylamine (0.15 mL, 1.12 mmol) were added. The solution continued to stir for eighteen hours. The solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate, water, 5% citric acid and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the amide as a light green oil (200 mg, 78%). MS (M+H): 458

후처리

  1. stirringto stir for eighteen hours
  2. customThe solution was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated sodium bicarbonate, water, 5% citric acid and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe slurry was filtered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a3a21df2449146c5b91de41cc724c2f2
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056110B2

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