Sodium Carbonate → [5-(2-Methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1783917ノート

反応式

HRID 1783917 の反応式
Br[C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[N:4][CH:3]=1.[CH3:25][O:26][C:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[CH:29][N:28]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C.O1CCOCC1>[CH3:25][O:26][C:27]1[CH:32]=[C:31]([C:2]2[N:7]3[N:8]=[CH:9][N:10]=[C:6]3[C:5]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)=[CH:14][CH:13]=3)=[N:4][CH:3]=2)[CH:30]=[CH:29][N:28]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 57590000(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

生成物 1

HCID 57590084[5-(2-Methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine収率 47%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 217120691,4-dioxane N,N-dimethylformamide溶媒

実験手順

This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (80 mg, 0.206 mmol), 2-methoxypyridine-4-boronic acid (63 mg, 0.412 mmol), Pd(PPh3)4 (0.052 mmol) and 1.5N Na2CO3 (1.1 mL, 1.65 mmol) in 2:1 DMF/dioxane (2.2 mL). The crude product is purified by silica gel column chromatography using 96:4 DCM:NH3 (7M in MeOH) and the fractions containing the desired product are combined and evaporated to afford the title compound (40 mg, 47%). HPLC (254 nm): Rt 2.26 min (65%).

後処理

  1. customThis compound may be prepared
  2. customThe crude product is purified by silica gel column chromatography
  3. additionNH3 (7M in MeOH) and the fractions containing the desired product
  4. customevaporated

出典と根拠

ORDレコード
ord-36290199d22b4ef481537591340ea0ba
出典データセット
uspto-grants-2009_03
特許番号
US07501411B2

反応ノート

読み込み中…