Trifluoroacetic acid → HCID 67497359, compound

HRID 1628232Notes

Reaction equation

HRID 1628232 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH:9][C:10](=[O:29])[C@@H:11]([NH:19][C:20]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:22][CH2:21]2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6]([C:30]2[N:34](C3CCCCO3)[N:33]=[CH:32][CH:31]=2)=[CH:5][N:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([NH:9][C:10](=[O:29])[C@@H:11]([NH:19][C:20]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:21][CH2:22]2)[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][C:6]([C:30]2[NH:34][N:33]=[CH:32][CH:31]=2)=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67497335HCID 67497335, compound

Product 1

HCID 67497359HCID 67497359, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 ml vial was added (2S)—N-(2-methoxy-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridin-3-yl)-3-phenyl-2-(1-(pyridin-2-yl)cyclopropylamino)propanamide 14.1.D (200 mg, 0.37 mmole), 8 ml of DCM and 2 ml of TFA. The reaction was stirred at room temperature for 2 hours then refluxed for 2 seconds at which time the solvent was removed with a stream of nitrogen. The crude was purified by reverse phase preparative HPLC to give (2S)—N-(2-methoxy-5-(1H-pyrazol-5-yl)pyridin-3-yl)-3-phenyl-2-(1-(pyridin-2-yl)cyclopropylamino)propanamide 14.1. (74 mg, 44% yield) LCMS ESI (pos.) m/e: 455.2 (M+1): 1H NMR (400 MHz, MeOH-d) δ ppm 8.59 (d, J=5.48 Hz, 1H), 8.56 (d, J=2.35 Hz, 1H,) 8.28 (d, J=2.35 Hz, 1H), 8.03-8.08 (m, 1H), 7.71 (d, J=2.35 Hz, 1H), 7.53-7.57 (m, 1H), 7.36 (d, J=8.22 Hz, 1H), 7.23-7.32 (m, 5H), 6.61 (d, J=2.35 Hz, 1H), 4.33 (t, J=7.63 Hz, 1H), 3.89 (s, 3H), 3.20 (d, J=7.83 Hz, 2H), 1.62-1.70 (m, 2H), 1.50-1.57 (m, 1H), 1.32 (ddd, J=10.17, 4.11, 2.15 Hz, 1H).

Workup

  1. temperaturethen refluxed for 2 seconds at which time the solvent
  2. customwas removed with a stream of nitrogen
  3. customThe crude was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-dc63962b2f264ad7a26290519bd2ff79
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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