3-Hydroxy-2,2-dimethylpropionic acid → HCID 178452761, compound

HRID 730777Notes

Reaction equation

HRID 730777 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:27]=[C:26]([NH2:28])[C:6]2[NH:7][C:8]([N:10]3[CH2:15][CH2:14][N:13]([C:16]4[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=4)[CH2:12][CH2:11]3)=[N:9][C:5]=2[CH:4]=1.[CH3:31][C:32]([CH3:38])([CH2:36][OH:37])[C:33](O)=[O:34].Cl.CN(C)CCCN=C=NCC>ClCCl>[OH:37][CH2:36][C:32]([CH3:38])([CH3:31])[C:33]([NH:28][C:26]1[C:6]2[NH:7][C:8]([N:10]3[CH2:11][CH2:12][N:13]([C:16]4[C:21]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:19]=[CH:18][N:17]=4)[CH2:14][CH2:15]3)=[N:9][C:5]=2[CH:4]=[C:3]([C:2]([F:1])([F:29])[F:30])[CH:27]=1)=[O:34]

Participants

5

Reactant 3

HCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178507663HCID 178507663, compound

Product 1

HCID 178452761HCID 178452761, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25-mL, round-bottom flask was added 5-(trifluoromethyl)-2-{4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}-1H-benzimidazol-7-amine (108 mg, 0.25 mmol, Example 58), 2,2-dimethyl-3-hydroxypropionic acid (47 mg, 0.4 mmol, Aldrich), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (76 mg, 0.4 mmol, Aldrich) and dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 36 h, washed with satd aq. NaHCO3 solution (10 mL), dried over Na2SO4, and filtered. The filtrate was evaporated and the residue was purified by silica gel column chromatography, eluting with 50% EtOAc/hexane to give the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: 531(M+1)

Workup

  1. washwashed with satd aq. NaHCO3 solution (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-2ea28508b12049d295caecba0826bd30
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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