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

HRID 1802002ノート

反応式

HRID 1802002 の反応式
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][CH:17]=[N: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][CH:17]=[N: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

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 57471876HCID 57471876、化合物

生成物 1

HCID 574718772-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-pyrazol-1-yl)phenylamino)pyrimidine-5-carboxamide収率 61.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-chloro-4-(3-fluoro-4-(1H-pyrazol-1-yl)phenylamino)pyrimidine-5-carboxylic acid (230 mg, 0.690 mmol) and HOBt (158 mg, 1.03 mmol) in DMF (4 mL), EDC (200 mg, 1.04 mmol) was added. The mixture was stirred at room temperature for 1.5 h. Ammonia (0.5 M in dioxane, 6.00 mL, 3.00 mmol) was added. It was stirred at room temperature overnight. Water and EtOAc were added. The organic phase was separated, washed with 1 N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-pyrazol-1-yl)phenylamino)pyrimidine-5-carboxamide (184 mg). MS 432.4 (M+H)

後処理

  1. stirringIt was stirred at room temperature overnight
  2. customThe organic phase was separated
  3. washwashed with 1 N HCl
  4. dry with materialwith 5% NaHCO3, dried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-983e2c14e60f470c8d2f1dcda9b19c02
出典データセット
uspto-grants-2013_01
特許番号
US08349860B2

反応ノート

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