Acetic Anhydride → HCID 24995324, compound

HRID 1914725Notes

Reaction equation

HRID 1914725 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:37][CH2:38][O:39][CH3:40])=[C:14]([NH:16][C:17]2[C:18]([NH:27][S:28]([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)(=[O:30])=[O:29])=[N:19][C:20]3[C:25]([N:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=1.CCN(CC)CC>C(Cl)Cl>[C:1]([N:34]1[CH2:35][CH2:36][CH:31]([S:28]([NH:27][C:18]2[C:17]([NH:16][C:14]3[CH:15]=[C:10]([O:9][CH3:8])[CH:11]=[CH:12][C:13]=3[CH2:37][CH2:38][O:39][CH3:40])=[N:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)(=[O:30])=[O:29])[CH2:32][CH2:33]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59353005HCID 59353005, compound

Product 1

HCID 24995324HCID 24995324, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetic anhydride (21 mg; 0.2 mmol; 1.2 eq) is added to a suspension of N-(3-{[5-methoxy-2-(2-methoxyethyl)phenyl]amino}quinoxalin-2-yl)piperidine-4-sulfonamide (100 mg; 0.17 mmol; 1 eq) in DCM (10 mL), followed by Et3N (0.06 mL; 0.43 mmol; 2.5 eq) and the reaction mixture is stirred at room temperature for 2 h. The solution is diluted to 30 mL with DCM, washed successively with 0.1 M HCl and brine, dried over MgSO4 and concentrated in vacuo to give a yellow solid. The residue is recrystallised from a mixture of DCM/n-pentane to afford 59 mg (67%) of the title compound as a pale yellow solid. 1H NMR (DMSO-d6) δ 12.25 (s, 1H), 9.15 (s, 1H), 7.95-7.81 (m, 2H), 7.50-7.44 (m, 1H), 7.37-7.26 (m, 2H), 7.22 (d, J=8.4 Hz, 1H), 6.71 (dd, J=8.4, 2.6 Hz, 1H), 4.53 (br d, J=12.8 Hz, 1H), 3.97 (br d, J=13.3 Hz, 1H), 3.78 (s, 3H), 3.60-3.36 (m, 3H), 3.25 (s, 3H), 3.10 (br t, J=12.0 Hz, 1H), 2.78 (t, J=6.0 Hz, 2H), 2.58 (br t, J=12.7 Hz, 1H), 2.19 (br d, J=12.7 Hz, 2H), 2.02 (s, 3H), 1.80-1.50 (m, 2H). HPLC (max plot) 99%; Rt 3.85 min. UPLC/MS (ES+) 512.2, (ES−) 512.3.

Workup

  1. washwashed successively with 0.1 M HCl and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a yellow solid
  5. customThe residue is recrystallised from a mixture of DCM/n-pentane

Sources & evidence

ORD record
ord-2a735e5a59524dabaaffae0deed9b5cc
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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