p-Toluenesulfonic acid monohydrate → HCID 44199442, compound

HRID 1907845Notes

Reaction equation

HRID 1907845 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[N:16]=[CH:17][C:18]3[N:23]=[N:22][N:21]([CH2:24][C:25]4[CH:26]=[C:27]5[C:32](=[CH:33][CH:34]=4)[N:31]=[CH:30][CH:29]=[CH:28]5)[C:19]=3[N:20]=2)[CH:12]=[N:11]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CO>[N:31]1[C:32]2[C:27](=[CH:26][C:25]([CH2:24][N:21]3[C:19]4[N:20]=[C:15]([C:13]5[CH:12]=[N:11][N:10]([CH2:9][CH2:8][OH:7])[CH:14]=5)[N:16]=[CH:17][C:18]=4[N:23]=[N:22]3)=[CH:34][CH:33]=2)[CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59627818HCID 59627818, compound

Product 1

HCID 44199442HCID 44199442, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-((5-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)methyl)quinoline (237 mg, 0.520 mmol) and TsOH.H2O (119 mg, 0.624 mmol) in MeOH (15 mL) was stirred for 3 h at room temperature. The solvent was removed under reduced pressure. The crude product was purified by reverse phase HPLC (CH3CN, H2O gradient plus 0.1% AcOH) to afford the title compound, after lyophilization, as a white powder (116 mg, 60%). 1H NMR (300 MHz, DMSO-d6) δ 3.72 (dd, 2H, J=10.8, 5.4 Hz), 4.18 (t, 2H, J=5.4 Hz), 4.90 (t, 1H, J=5.3 Hz), 6.06 (s, 2H), 7.47 (m, 1H), 7.76 (m, 1H), 7.93-7.97 (m, 2H), 8.12 (m, 1H), 8.31 (m, 1H), 8.45 (s, 1H), 8.90 (m, 1H), 9.64 (s, 1H); LCMS (APCI) m/z 373.2 (M+H+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe crude product was purified by reverse phase HPLC (CH3CN, H2O gradient plus 0.1% AcOH)

Sources & evidence

ORD record
ord-f90aeb1ce1b64b8993b67a9122f8a240
Source dataset
uspto-grants-2013_12
Patent number
US08598184B2

Reaction notes

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