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 30813Notes

Reaction equation

HRID 30813 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d034d5bc5a394e5480b48fd4fcafef94
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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