Pyrrolidine → HCID 60054651, compound

HRID 1792873Notes

Reaction equation

HRID 1792873 reaction equation
C([N:4]1[C@:8]2([C@H:12]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[CH2:11][N:10]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:9]2)[C:7](=[O:28])[N:6]([C:29]2[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=2)[C:5]1=[O:37])(=O)C.N1CCCC1>C1COCC1>[CH2:21]([N:10]1[CH2:11][C@@H:12]([C:13]2[CH:14]=[CH:15][C:16]([C:17]#[N:18])=[CH:19][CH:20]=2)[C@:8]2([NH:4][C:5](=[O:37])[N:6]([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=3)[C:7]2=[O:28])[CH2:9]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 60054667HCID 60054667, compound

Product 1

HCID 60054651HCID 60054651, compoundYield 113.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 11 (8.9 g, 16.7 mmol), TEA (3.8 ml) and pyrrolidine (2.2 ml) in THF (270 ml) was refluxed for 2 h 30 min. The mixture was concentrated in vacuo and taken into DCM, then washed with water. The organic layer was dried over MgSO4 and concentrated. The resulting solid was chromatographed over silica gel (eluent: DCM/MeOH 95/5) to yield the above-titled compound (9.3 g) as a white solid (mp=200° C.). 1H NMR (DMSO-d6): 9.32 (1H, br s), 7.84 (2H, d, J=8.2 Hz), 7.60 (1H, m), 7.25–7.45 (7H, m), 6.74 (2H, d, J=1.9 Hz), 3.65–3.9 (3H, m), 3–3.3 (4H, m).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washwashed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting solid was chromatographed over silica gel (eluent: DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-08d22c3fc77948e883a615f5285a17f6
Source dataset
uspto-grants-2006_07
Patent number
US07078420B2

Reaction notes

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