Acetic Acid → N-[4-({2-[(3-isopropylphenyl)amino]-1-methyl-1H-benzimidazol-5-yl}oxy)pyridin-2-yl]-2-(1-methylpiperidin-4-yl)acetamide

HRID 1963731ノート

反応式

HRID 1963731 の反応式
[CH:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29](=[O:37])[CH2:30][CH:31]5[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]5)[CH:23]=4)=[CH:20][C:13]=3[N:12]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[C:38](O)(=O)C.C=O.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.CO>[CH:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29](=[O:37])[CH2:30][CH:31]5[CH2:32][CH2:33][N:34]([CH3:38])[CH2:35][CH2:36]5)[CH:23]=4)=[CH:20][C:13]=3[N:12]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 59790190N-(4-(2-(3-isopropylphenylamino)-1-methyl-1H-benzo[d]imidazol-5-yloxy)pyridin-2-yl)-2-(piperidin-4-yl)acetamide

生成物 1

HCID 59790284N-[4-({2-[(3-isopropylphenyl)amino]-1-methyl-1H-benzimidazol-5-yl}oxy)pyridin-2-yl]-2-(1-methylpiperidin-4-yl)acetamide

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To the mixture containing N-(4-(2-(3-isopropylphenylamino)-1-methyl-1H-benzo[d]imidazol-5-yloxy)pyridin-2-yl)-2-(piperidin-4-yl)acetamide (1 eq), glacial acetic acid (2 eq), and formaline (7.5 eq) in tetrahydrofuran:methanol (1:1) was added sodium cyanoborohydride (2 eq) and stirred at room temperature for one hour. Reaction neutralized with saturated sodium carbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give crude product. Purification by HPLC to yield N-[4-({2-[(3-isopropylphenyl)amino]-1-methyl-1H-benzimidazol-5-yl}oxy)pyridin-2-yl]-2-(1-methylpiperidin-4-yl)acetamide.

後処理

  1. customReaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give crude product
  7. customPurification by HPLC

出典と根拠

ORDレコード
ord-2d7d305e54034ee8851e5e02342817d1
出典データセット
uspto-grants-2013_04
特許番号
US08415382B2

反応ノート

読み込み中…