HCID 86683606, compound → HCID 67256414, compound

HRID 1509205Notes

Reaction equation

HRID 1509205 reaction equation
[O:1]=[S:2]1(=[O:42])[N:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:6]2[CH:14]=[C:15]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4([NH:28]C(=O)OC(C)(C)C)[CH2:27][CH2:26][CH2:25]4)=[CH:20][CH:19]=3)=[N:17][C:5]=2[O:4][CH2:3]1>C(O)(C(F)(F)F)=O>[NH2:28][C:24]1([C:21]2[CH:22]=[CH:23][C:18]([C:16]3[C:15]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)=[CH:14][C:6]4[N:7]([C:8]5[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=5)[S:2](=[O:1])(=[O:42])[CH2:3][O:4][C:5]=4[N:17]=3)=[CH:19][CH:20]=2)[CH2:25][CH2:26][CH2:27]1

Participants

3

Reactant 1

HCID 86683606HCID 86683606, compound

Product 1

HCID 67256414HCID 67256414, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (1-(4-(2,2-dioxido-7-phenyl-1-(pyridin-3-yl)-1H-pyrido[3,2-e][1,3,4]oxathiazin-6-yl)phenyl)cyclobutyl)carbamate (40 mg, 0.068 mmol) was dissolved in TFA (3 mL) and stirred for 30 seconds. The solution was immediately concentrated to dryness under reduced pressure. The residue was dissolved in diethyl ether (˜3 mL) and concentrated to dryness under reduced pressure three times. The residue was then slurried in diethyl ether (3 mL) and after settling the supernatant solvent removed by pipette. This was repeated three times. The remaining solvent was removed by freeze drying overnight to give the desired compound as an off-white solid (23 mg, 56% yield). 1H-NMR (500 MHz, MeOD) δ 8.70 (1H, d), 8.65 (1H, dd), 8.00 (1H, dd), 7.61 (1H, dd), 7.44 (2H, d), 7.38 (2H, d), 7.17-7.25 (3H, m), 7.09 (1H, s), 7.06 (2H, d), 5.67 (2H, s), 2.68-2.77 (2H, m), 2.50-2.59 (2H, m), 2.14-2.25 (1H, m), 1.87-2.00 (1H, m). LCMS (Method A) RT=4.00 min, M+2H+=486.07.

Workup

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

Sources & evidence

ORD record
ord-434d8eb1e8564b68a3fc12f10e977d4d
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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