Morpholine → HCID 22277823, compound

HRID 1064015Notes

Reaction equation

HRID 1064015 reaction equation
[O:1]=[S:2]1(=[O:27])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=O)[CH2:20][CH2:19]3)=[O:17])[CH:13]=[CH:14][C:3]1=2.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CCN=C=NCCCN(C)C.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[O:1]=[S:2]1(=[O:27])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH:15][C:16]([N:18]3[CH2:19][CH2:20][CH:21]([C:24]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[O:26])[CH2:22][CH2:23]3)=[O:17])[CH:13]=[CH:14][C:3]1=2

Participants

6

Reactant 4

HCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22277802HCID 22277802, compound

Product 1

HCID 22277823HCID 22277823, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,5-Dioxo-2-(4-carboxypiperidinocarbonylamino)dibenzothiophene (Example 84; 75 mg, 0.19 mmol), DMF (2.5 ml), morpholine (16.5 mg, 0.19 mmol), EDAC (44 mg, 0.23 mmol), 1-hydroxybenzotriazole hydrate (25.65 mg, 0.19 mmol) were stirred together for 18 hours. The solvent was removed under vacuum and the residue partitioned between H2O/EtOAc. The organic layers were washed with water, saturated aqueous NaHCO3 then brine, and then dried, filtered and evaporated to an amorphous solid. NMR: 9.08 (s, 1H)) 8.21 (d, 1H), 7.93 (m, 2H), 7.79 (m, 2H), 7.65 (m, 2H), 4.14 (m, 2H), 3.52 (m, 6H), 3.45 (m, 2H), 2.92 (m, 3H), 1.68 (m, 2H), 1.53 (m, 2H); m/z 456.73.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue partitioned between H2O/EtOAc
  3. washThe organic layers were washed with water, saturated aqueous NaHCO3
  4. dry with materialbrine, and then dried
  5. filtrationfiltered
  6. customevaporated to an amorphous solid

Sources & evidence

ORD record
ord-5dd6c609e2ed4ca4afdf2cea22259aef
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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