HCID 123769430, compound → HCID 53262182, compound

HRID 1509180Notes

Reaction equation

HRID 1509180 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:20][C:21]4[N:26]([CH2:27][CH2:28][C:29]#[N:30])[C:25](=[O:31])[CH2:24][O:23][C:22]=4[N:32]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[CH:20][C:21]4[N:26]([CH2:27][CH2:28][C:29]#[N:30])[C:25](=[O:31])[CH2:24][O:23][C:22]=4[N:32]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 123769430HCID 123769430, compound

Product 1

HCID 53262182HCID 53262182, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl(1-(4-(1-(2-cyanoethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (15 mg, 0.029 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 (0.5 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 (12 mg). 1H NMR (500 MHz, CH3OD) 7.77 (1H, s), 7.43 (2H, d), 7.39 (2H, d), 7.3 (3H, m), 7.27 (2H, m), 4.99 (2H, s), 4.37 (2H, t), 2.94 (2H, t), 2.73-2.79 (2H, m), 2.55-2.61 (2H, m), 2.2-2.27 (1H, m), 1.93-1.99 (1H, m). LCMS (Method A): RT=3.73 min, M+H+=425.

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-f05e6ccc162142e0acb0441ea27adde7
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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