Trifluoroacetic acid → HCID 59394712, compound

HRID 45172Notes

Reaction equation

HRID 45172 reaction equation
[CH:1]1([C:4]2[N:8]([CH3:9])[N:7]=[C:6]([NH:10][C:11]([N:13]3[C:21]4[C:16](=[CH:17][C:18]([O:22][C:23]5[CH:28]=[CH:27][N:26]=[C:25]([CH2:29][N:30](C)[C:31](=O)OC(C)(C)C)[CH:24]=5)=[CH:19][CH:20]=4)[CH:15]=[CH:14]3)=[O:12])[CH:5]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([C:4]2[N:8]([CH3:9])[N:7]=[C:6]([NH:10][C:11]([N:13]3[C:21]4[C:16](=[CH:17][C:18]([O:22][C:23]5[CH:28]=[CH:27][N:26]=[C:25]([CH2:29][NH:30][CH3:31])[CH:24]=5)=[CH:19][CH:20]=4)[CH:15]=[CH:14]3)=[O:12])[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59394157HCID 59394157, compound

Product 1

HCID 59394712HCID 59394712, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (4-(1-(5-cyclopropyl-1-methyl-1H-pyrazol-3-ylcarbamoyl)-1H-indol-5-yloxy)pyridin-2-yl)methyl(methyl)carbamate (0.124 g, 0.240 mmol) in DCM (5 ml) is added TFA (2 ml, 0.240 mmol). The reaction is stirred for approximately 30 minutes and then concentrated in vacuo to near dryness. The residue is dissolved in DCM, diluted with water and neutralized via the addition of saturated aqueous NaHCO3. The resulting layers are then separated and the aqueous layer is extracted twice with DCM. The organic layers are combined dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue is purified via FCC (0-15% MeOH/DCM) to provide the title compound. MS (ESI) m/z 417.2 (M+1). 1HNMR (400 MHz, DMSO-d6) δ ppm 0.64-0.70 (m, 2 H)0.96-1.02 (m, 2 H)1.87-1.96 (m, 1 H)2.27 (s, 3 H)3.71 (s, 2 H)3.80 (s, 3 H) 6.16 (d, J=0.51 Hz, 1 H)6.73 (dd, J=3.79, 0.51 Hz, 1 H)6.80 (dd, J=5.56, 2.53 Hz, 1 H)6.93 (d, J=2.02 Hz, 1 H)7.09 (dd, J=8.97, 2.40 Hz, 1 H)7.42 (d, J=2.27 Hz, 1 H)8.17 (d, J=3.54 Hz, 1 H) 8.33 (d, J=8.84 Hz, 1 H)8.36 (d, J=5.81 Hz, 1 H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in DCM
  3. additiondiluted with water and neutralized via the addition of saturated aqueous NaHCO3
  4. customThe resulting layers are then separated
  5. extractionthe aqueous layer is extracted twice with DCM
  6. dry with materialThe organic layers are combined dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue is purified via FCC (0-15% MeOH/DCM)

Sources & evidence

ORD record
ord-bb89e02a078f4ad1b948e21ecfa3524d
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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