N-Hydroxyacetamidine → N-ethanimidoyl-3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzamide

HRID 216144

반응식

HRID 216144 반응식
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)[CH:6]=[C:5]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:4]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:60](=[N:63]O)([NH2:62])[CH3:61]>CN(C)C=O.O>[NH:62]=[C:60]([NH:63][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][CH:17]=[C:9]([C:7]2[CH:6]=[C:5]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:4]=[C:3]([O:2][CH3:1])[N:8]=2)[CH:10]=1)[CH3:61]

참가 물질

7

반응물 4

HCID 30926N-HydroxyacetamidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 116033013-{2-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

생성물 1

HCID 148920926N-ethanimidoyl-3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzamide수율 69%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid (200 mg, 0.53 mmol, Example 35(a)] in dimethylformamide (1.75 mL) is added diisopropylethylamine (0.23 mL, 1.33 mmol) followed by TBTU (205 mg, 0.64 mmol). Stirred the solution for 15 minutes before adding acetamide oxime (59 mg, 0.8 mmol). After 4 hours of stirring at ambient temperature the mixture is diluted with water (20 mL) and extracted twice with EtOAc (20 mL). The combined organic extracts are washed three times with water (20 mL), with brine (20 mL), dried over magnesium sulfate, filtered and concentrated by rotary evaporator to provide N-(1-imino-ethyl)-3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzamide [60 mg, 69%, Intermediate (45)].

후처리

  1. stirringAfter 4 hours of stirring at ambient temperature the mixture
  2. extractionextracted twice with EtOAc (20 mL)
  3. washThe combined organic extracts are washed three times with water (20 mL)
  4. dry with materialwith brine (20 mL), dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporator

출처 및 근거

ORD 기록
ord-7f62c8cd99364990a4f394b63ea95e98
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193183B2

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