Acetic Anhydride → HCID 71610199, compound

HRID 1479057Notes

Reaction equation

HRID 1479057 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C:9]1[C:17]([CH3:18])=[N:16][C:15]2[N:11]([N:12]=[C:13]3[CH2:21][N:20]([C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[O:23])[CH2:19][C:14]3=2)[C:10]=1[CH3:37]>C(Cl)Cl>[Cl:8][C:9]1[C:17]([CH3:18])=[N:16][C:15]2[N:11]([N:12]=[C:13]3[CH2:21][N:20]([C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH:31]4[CH2:36][CH2:35][N:34]([C:1](=[O:3])[CH3:2])[CH2:33][CH2:32]4)=[O:23])[CH2:19][C:14]3=2)[C:10]=1[CH3:37]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 71610126HCID 71610126, compound

Product 1

HCID 71610199HCID 71610199, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetic anhydride (27 μL; 0.28 mmol; 1.2 eq.) was added to a suspension of Example 3 (100 mg; 0.23 mmol; 1 eq.) and TEA (82 μL; 0.59 mmol; 2.5 eq.) in DCM (3 mLl) and the resulting mixture was stirred at room temperature for 2 hours. The solution was diluted with DCM, washed with 0.1M HCl and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (72 mg, 66%) as a white solid. 1H NMR (CDCl3) δ 7.42-7.35 (m, 2H), 7.11-7.04 (m, 1H), 7.02-6.97 (m, 1H), 5.01-4.99 (m, 2H), 4.71-4.58 (m, 3H), 3.75-3.68 (m, 1H), 3.60-3.46 (m, 2H), 3.40-3.32 (m, 1H), 2.91 (s, 2H), 2.85 (s, 1H), 2.69 (s, 1H), 2.62 (s, 2H), 2.04 (s, 3H), 1.90-1.74 (m, 4H). HPLC (max plot) 99.4%, Rt 3.16 min. UPLC/MS: (MS+) 468.4 ([M+H]+).

Workup

  1. washwashed with 0.1M HCl and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by mass

Sources & evidence

ORD record
ord-a169db3cc4874d44996bcefcd4218398
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

Loading…