Triethylamine → n-(2-(Dimethylamino)ethyl)-n-methyl-4-(3-(quinolin-6-ylmethyl)-3h-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzamide

HRID 15986

반응식

HRID 15986 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:25]1[C:34]2[C:29](=[CH:30][C:31]([CH2:35][N:36]3[C:44]4[C:39](=[N:40][CH:41]=[C:42]([C:45]5[CH:53]=[CH:52][C:48]([C:49]([OH:51])=O)=[CH:47][CH:46]=5)[N:43]=4)[N:38]=[N:37]3)=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1.[CH3:54][N:55]([CH3:60])[CH2:56][CH2:57][NH:58][CH3:59].C(N(CC)CC)C>CN(C=O)C>[CH3:54][N:55]([CH3:60])[CH2:56][CH2:57][N:58]([CH3:59])[C:49](=[O:51])[C:48]1[CH:47]=[CH:46][C:45]([C:42]2[N:43]=[C:44]3[N:36]([CH2:35][C:31]4[CH:30]=[C:29]5[C:34](=[CH:33][CH:32]=4)[N:25]=[CH:26][CH:27]=[CH:28]5)[N:37]=[N:38][C:39]3=[N:40][CH:41]=2)=[CH:53][CH:52]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593418624-(3-(Quinolin-6-ylmethyl)-3h-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzoic acid

생성물 1

HCID 45381021n-(2-(Dimethylamino)ethyl)-n-methyl-4-(3-(quinolin-6-ylmethyl)-3h-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzamide수율 57.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

HATU (82 mg, 0.22 mmol) was added to a mixture of 4-(3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzoic acid (75 mg, 0.20 mmol), N1,N1,N2-trimethylethane-1,2-diamine (22 mg, 0.22 mmol) and triethylamine (0.060 mL, 0.43 mmol) in DMF (2.0 mL). After stirring for 18 hours, the reaction was partitioned between dichloromethane:ethanol (9:1) and water. The organic layer was separated, dried over Na2SO4, filtered and concentrated by rotary evaporation to afford 108 mg of crude material. The material was purified by pre-HPLC to give N-(2-(dimethylamino)ethyl)-N-methyl-4-(3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzamide (54 mg, yield 48%).

후처리

  1. customthe reaction was partitioned between dichloromethane:ethanol (9:1) and water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customto afford 108 mg of crude material
  7. customThe material was purified by pre-HPLC

출처 및 근거

ORD 기록
ord-ca7cbd2bacca4b64818d67886f66b7f8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732604B2

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