Sodium Hydroxide → HCID 135808011, compound

HRID 238219Notes

Reaction equation

HRID 238219 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([NH:21][C:22]3[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=3[C:24]([NH2:26])=[O:25])=O)[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][C:19]3[NH:26][C:24](=[O:25])[C:23]4[C:22](=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:21]=3)[CH2:16][CH2:17]2)(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22200422HCID 22200422, compound

Product 1

HCID 135808011HCID 135808011, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-{2-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-acetylamino}-benzamide (432 mg, 1 mmol), 1N sodium hydroxide solution (5 mL) and 1,4-dioxane (5 mL) was stirred a room temperature for 1 day. The reaction mixture was concentrated to approximately half the volume and then neutralized with 1N HCl solution. The product precipitated and was collected by filtration as a white solid (306 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 8.26 (dd, J=8.0, 1.3 Hz, 1H), 7.79 (t, J=8.4 Hz, 1H), 7.73 (dt, J=9.5, 2.5 Hz, 2H), 7.68 (d, J=7.7 Hz, 1H), 7.51 (t, J=8.1 Hz, 1H), 7.08 (dt, J=9.5, 2.4 Hz, 2H), 3.94 (s, 3H), 3.65 (s, 2H), 3.11 (m, 4H), 2.75 (t, J=4.9 Hz, 4H); HPLC ret. time 2.59 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 415.3 (M+1)+.

Workup

  1. concentrationThe reaction mixture was concentrated to approximately half the volume
  2. customThe product precipitated
  3. filtrationwas collected by filtration as a white solid (306 mg, 74%)
  4. customHPLC ret. time 2.59 min, 10-99% CH3CN, 5 min

Sources & evidence

ORD record
ord-6a68ee2c8827467bb44a77979e95ad6c
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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