Trifluoroacetic acid → HCID 178480425, compound

HRID 2274427Notes

Reaction equation

HRID 2274427 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[C:37]([N:38]2[CH2:44][CH2:43][CH2:42][N:41]([CH3:45])[CH2:40][CH2:39]2)=[CH:36][C:12]2[NH:13][C:14]([C:16]3[C:20]([NH:21][C:22]([N:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:23])=[CH:19][N:18](C4CCCCO4)[N:17]=3)=[N:15][C:11]=2[CH:10]=1>ClCCl>[F:8][C:9]1[C:37]([N:38]2[CH2:44][CH2:43][CH2:42][N:41]([CH3:45])[CH2:40][CH2:39]2)=[CH:36][C:12]2[NH:13][C:14]([C:16]3[C:20]([NH:21][C:22]([N:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]4)=[O:23])=[CH:19][NH:18][N:17]=3)=[N:15][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178480422HCID 178480422, compound

Product 1

HCID 178480425HCID 178480425, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

0.5 mL of trifluoroacetic acid is added to a solution of 60 mg of N-[3-[5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-1H-benzimidazol-2-yl]-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]piperidine-1-carboxamide in solution in 1 mL of dichloromethane. The reaction medium is stirred at 22° C. for 16 hours. The reaction medium is concentrated under vacuum in a rotary evaporator. After evaporation, the reaction crude is purified by flash chromatography. The elution is carried out with pure dichloromethane and then with a mixture of dichloromethane containing 5% of ammoniacal methanol. 29 mg of N-{3-[5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}piperidine-1-carboxamide are obtained in the form of a yellow solid. 1H NMR (400 MHz, DMSO-d6, δ in ppm): 1.42 to 2.27 (m, 8H); 2.90 (s, 3H); from 3.18 to 3.65 (m, 12H); 7.20 (d, J=7.0 Hz, 1H); 7.56 (d, J=12.0 Hz, 1H); 8.00 (s, 1H). ES mass spectrum: m/z=439 (M−H)—base peak.

Workup

  1. concentrationThe reaction medium is concentrated under vacuum in a rotary evaporator
  2. customAfter evaporation
  3. customthe reaction crude
  4. customis purified by flash chromatography
  5. washThe elution
  6. additionwith a mixture of dichloromethane containing 5% of ammoniacal methanol

Sources & evidence

ORD record
ord-a8acd61ab7b04bd4ae05b29641420802
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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