1,2-Dichloroethane → 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxamide

HRID 1802015노트

반응식

HRID 1802015 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)=[C:11]([F:20])[CH:10]=2)[C:5]([C:21]([OH:23])=O)=[CH:4][N:3]=1.[CH:24]1[CH:25]=[CH:26][C:27]2[N:32]([OH:33])[N:31]=[N:30][C:28]=2[CH:29]=1.C(Cl)CCl.[NH3:38]>CN(C=O)C.CCOC(C)=O.O>[N:32]1([O:33][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH:19]=[CH:18][N:17]=[CH:16]4)=[C:11]([F:20])[CH:10]=3)[C:5]([C:21]([NH2:38])=[O:23])=[CH:4][N:3]=2)[C:27]2[CH:26]=[CH:25][CH:24]=[CH:29][C:28]=2[N:30]=[N:31]1

참가 물질

8

반응물 4

HCID 111,2-Dichloroethane2회HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 574718862-chloro-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxylic acid

생성물 1

HCID 574718872-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxamide수율 66.1%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-chloro-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxylic acid (68 mg, 0.20 mmol) and HOBt (63 mg, 0.41 mmol) in DMF (2 mL), EDC (60 mg, 0.31 mmol) was added. The mixture was stirred at room temperature for 1.5 h. Ammonia (0.5 M in dioxane, 0.800 mL, 0.40 mmol) was added. It was stirred at room temperature overnight. More EDC (100 mg, 0.52 mmol) was added. It was stirred for another 24 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 2-(1H-benzo[d][1,2,3]triazol-1-yl oxy)-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxamide (57 mg). MS 432.2 (M+H)

후처리

  1. stirringIt was stirred at room temperature overnight
  2. stirringIt was stirred for another 24 h
  3. customThe organic phase was separated
  4. washwashed with 5% NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-53746a7a88914f4782fe79da9907ce25
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349860B2

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