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 30813노트

반응식

HRID 30813 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

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. HPLC=3.51 min; MS: MH+=513.

후처리

  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

출처 및 근거

ORD 기록
ord-d034d5bc5a394e5480b48fd4fcafef94
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423150B2

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