Trifluoroacetic acid → HCID 178464315, compound

HRID 2274385Notes

Reaction equation

HRID 2274385 reaction equation
[CH2:1]([N:3]([CH2:34][CH3:35])[C:4]([NH:6][C:7]1[C:8]([C:18]2[NH:22][C:21]3[CH:23]=[C:24]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[C:25]([F:27])=[CH:26][C:20]=3[N:19]=2)=[N:9][N:10](C2CCCCO2)[CH:11]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:34]([N:3]([CH2:1][CH3:2])[C:4]([NH:6][C:7]1[C:8]([C:18]2[NH:22][C:21]3[CH:23]=[C:24]([N:28]4[CH2:29][CH2:30][O:31][CH2:32][CH2:33]4)[C:25]([F:27])=[CH:26][C:20]=3[N:19]=2)=[N:9][NH:10][CH:11]=1)=[O:5])[CH3:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178464304HCID 178464304, compound

Product 1

HCID 178464315HCID 178464315, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 95 mg of 1,1-diethyl-3-[3-(5-fluoro-6-morpholin-4-yl-1H-benzimidazol-2-yl)-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]urea in 3 mL of dichloromethane, to which 750 μL of trifluoroacetic acid are added, is stirred at ambient temperature for 48 hours. The reaction medium is concentrated to dryness and then purified by preparative LC/MS: injection of the product in 2.5 mL of DMSO, elution with a gradient of 5% to 95% of acetonitrile in water, containing respectively 0.07% of TFA, in 12 minutes. 49 mg of 1,1-diethyl-3-[3-(5-fluoro-6-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]urea are isolated in the form of a trifluoroacetate salt. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.23 (t, J=7.0 Hz, 6H); 3.00 (m, 4H); 3.41 (m partially masked, 4H); 3.78 (m, 4H); 7.11 (broad d, J=8.0 Hz, 1H); 7.33 (broad d, J=12.0 Hz, 1H); 7.99 (s, 1H); 9.78 (s, 1H); 13.0 (broad m, 2H).

Workup

  1. concentrationThe reaction medium is concentrated to dryness
  2. custompurified by preparative LC/MS
  3. washinjection of the product in 2.5 mL of DMSO, elution with a gradient of 5% to 95% of acetonitrile in water
  4. additioncontaining respectively 0.07% of TFA
  5. waitin 12 minutes

Sources & evidence

ORD record
ord-21e81d84098f4bdc8265026247362ad3
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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