Acetic Acid → HCID 22348062, compound

HRID 897239Notes

Reaction equation

HRID 897239 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([NH:28][C:29]4[C:38]5[C:33](=[CH:34][CH:35]=[C:36]([O:39][CH3:40])[CH:37]=5)[O:32][C:31](=[O:41])[CH:30]=4)[CH2:24][CH2:23]3)=[CH:20][C:15]=2[O:14][CH2:13]1.[Cl:42]N1C(=O)CCC1=O.C(O)(=O)C>C(#N)C>[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([NH:28][C:29]4[C:38]5[C:33](=[CH:34][CH:35]=[C:36]([O:39][CH3:40])[CH:37]=5)[O:32][C:31](=[O:41])[C:30]=4[Cl:42])[CH2:24][CH2:23]3)=[CH:20][C:15]=2[O:14][CH2:13]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 22348012HCID 22348012, compound

Product 1

HCID 22348062HCID 22348062, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 4-(1-Benzo[1,3]dioxol-5-ylmethyl-piperidin-4-ylamino)-6-methoxy-chromen-2-one para-toluene sulfonic acid salt (0.025 g, 0.043 mmol), N-chlorosuccinimide (0.0061 g, 0.046 mmol), and 0.2 mL Acetic Acid were shaken at room temperature overnight. Solution was diluted with Acetonitrile and purified on a C-18 RP HPLC. Product fractions were combined, treated with K2CO3, extracted with CH2Cl2, dried over sodium sulfate and concentrated to dryness to give the title compound as an off white solid. MS ESI(+)Q1MS m/z 451 (M−H)+; 1H NMR (300 MHz, CDCl3) δ ppm partially buried 1.47-1.78 (m, 2H), 2.03-2.21 (m, 4H), 2.8-2.91 (br d, 2H), 3.39-3.46 (s, 2H), 3.8-3.87 (s, 3H), 4.01-4.13 (m, 1H), 4.83-4.91 (br s, 1H), 5.93-5.97 (s, 2H), 6.71-6.78 (m, 2H), 6.83-6.86 (s, 1H), 7.05-7.16 (m, 2H), 7.27-7.36 (d, 1H).

Workup

  1. custompurified on a C-18 RP HPLC
  2. additiontreated with K2CO3
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cafe0df0d62a467b8d5f4cc59d2e6719
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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