HCID 86683527, compound → HCID 53261795, compound

HRID 1509075Notes

Reaction equation

HRID 1509075 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]3[CH:8]=[C:9]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:10]([C:15]4[CH:20]=[CH:19][C:18]([C:21]5([NH:25]C(=O)OC(C)(C)C)[CH2:24][CH2:23][CH2:22]5)=[CH:17][CH:16]=4)=[N:11][C:12]=3[CH2:13][CH2:14][C:5]=2[CH:4]=[N:3]1>C(O)(C(F)(F)F)=O>[CH3:1][N:2]1[C:6]2[C:7]3[CH:8]=[C:9]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:10]([C:15]4[CH:20]=[CH:19][C:18]([C:21]5([NH2:25])[CH2:22][CH2:23][CH2:24]5)=[CH:17][CH:16]=4)=[N:11][C:12]=3[CH2:13][CH2:14][C:5]=2[CH:4]=[N:3]1

Participants

3

Reactant 1

HCID 86683527HCID 86683527, compound

Product 1

HCID 53261795HCID 53261795, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl (1-(4-(1-methyl-8-phenyl-4,5-dihydro-1H-pyrazolo[3,4-f]quinolin-7-yl)phenyl)cyclobutyl)carbamate (3 mg, 0.006 mmol) was dissolved in TFA (0.5 mL) and stirred for 30 seconds. The solution was immediately concentrated to dryness under reduced pressure. The residue was dissolved in diethyl ether (˜1 mL) and concentrated to dryness under reduced pressure three times. The residue was then slurried in diethyl ether (1 mL) and after settling the supernatant solvent removed by pipette. This was repeated three times. The remaining solvent was removed under reduced pressure and dried to give the desired product as an off-white solid (0.65 mg, 22% yield). 1H NMR (500 MHz, CH3OD) 8.06 (s, 1H), 7.50 (d, 2H), 7.43 (d, 3H), 7.27-7.36 (br m, 5H), 4.19 (s, 1H), 3.22 (t, 2H), 2.93 (t, 2H), 2.73-2.83 (br m, 2H), 2.54-2.66 (br m, 2H), 2.18-2.33 (br m, 1H), 1.92-2.03 (br m, 1H). LCMS (Method A): RT=4.21 min, M+H+=407

Workup

  1. concentrationThe solution was immediately concentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in diethyl ether (˜1 mL)
  3. concentrationconcentrated to dryness under reduced pressure three times
  4. customremoved by pipette
  5. customThe remaining solvent was removed under reduced pressure
  6. customdried

Sources & evidence

ORD record
ord-4557d447323d47e08634ee743da4a434
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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