Triethylamine → HCID 66652833, compound

HRID 2074096Notes

Reaction equation

HRID 2074096 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([N:15]3[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17][CH2:16]3)=[O:14])[N:10]=[C:9]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH:8]=2)=[CH:4][CH:3]=1.[CH2:30](N(CC)CC)C.[S:37](Cl)(Cl)(=[O:39])=[O:38]>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([N:15]3[CH2:16][CH2:17][CH:18]([NH:21][S:37]([CH3:30])(=[O:39])=[O:38])[CH2:19][CH2:20]3)=[O:14])[N:10]=[C:9]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)[CH:8]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 67092302HCID 67092302, compound

Product 1

HCID 66652833HCID 66652833, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-amine (1.13 g, 2.87 mmol) in CH2Cl2 (10 mL) was added triethylamine (442.0 μL, 3.20 mmol) followed by sulfonyl chloride (223.0 μL, 2.87 mmol) and the reaction stirred at 25° C. for 1 hour. The solvent was removed in vacuo, and the residue was taken up in EtOAc (200 mL) and washed with water (2×50 mL), brine (100 mL), dried over MgSO4, filtered and stripped. The resulting gum was azeotroped with EtOAc (2×200 mL) to yield a white solid. The white solid was taken up in MeOH (25 mL) with heating, and left to crystallize overnight to afford small colorless needles. The MeOH was decanted and the crystals washed with MeOH (3×15 mL), EtOAc (3×30 mL) and finally hexane (2×25 mL, then 100 mL) and dried at room temperature to yield the title compound as white needles, 968 mg, 72 %. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.53 (d, 2 H), 7.65 (d, 2 H), 7.30 (t, 2 H), 7.20 (s, 1 H), 7.15 (t, 2 H), 6.52 (s, 1 H), 5.18 (q, 2 H), 4.10 (d, 1 H), 3.93 (s, 2 H), 3.83 (d, 1 H), 3.36-3.46 (m, 1 H), 3.17 (t, 1 H), 2.94 (s, 3 H), 2.80 (t, 1 H), 1.79-1.92 (m, 2 H), 1.41-1.52 (m, 1 H), 1.23-1.34 (m, 1 H); m/z (APCI+) for C23H26N5O3FS 472.1 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with water (2×50 mL), brine (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe resulting gum was azeotroped with EtOAc (2×200 mL)
  6. customto yield a white solid
  7. temperaturewith heating
  8. waitleft
  9. customto crystallize overnight
  10. customto afford small colorless needles
  11. customThe MeOH was decanted
  12. washthe crystals washed with MeOH (3×15 mL), EtOAc (3×30 mL) and finally hexane (2×25 mL
  13. custom100 mL) and dried at room temperature

Sources & evidence

ORD record
ord-ad45993dfb194edd9ce525f21d3a7883
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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