Triphenylphosphine → 1-(6-Chloro-4-cyanopyridin-2-yl)piperidin-4-yl 3,4-dichloro-5-methyl-1H-pyrrole-2-carboxylate

HRID 2234042Notes

Reaction equation

HRID 2234042 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9](NC1CCN(C2C=CN=C(Cl)N=2)CC1)=[O:10].[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([N:34]2[CH2:39][CH2:38][CH:37]([OH:40])[CH2:36][CH2:35]2)[N:33]=1)[C:29]#[N:30].CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([O:40][CH:37]1[CH2:38][CH2:39][N:34]([C:32]2[CH:31]=[C:28]([C:29]#[N:30])[CH:27]=[C:26]([Cl:25])[N:33]=2)[CH2:35][CH2:36]1)=[O:10]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 830734032-Chloro-6-(4-hydroxypiperidin-1-yl)isonicotinonitrile2×HCID 866083433,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide2×

Product 1

HCID 866082941-(6-Chloro-4-cyanopyridin-2-yl)piperidin-4-yl 3,4-dichloro-5-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dichloro-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 3, 164 mg, 0.84 mmol) was dissolved in anhydrous THF (3 ml). 2-Chloro-6-(4-hydroxypiperidin-1-yl)isonicotinonitrile (Intermediate 26), 200 mg, 0.84 mmol) was added, then DEAD (133 μl, 0.84 mmol) was added dropwise followed by triphenylphosphine (221 mg, 0.84 mmol). The mixture was stirred at room temperature for 18 h. The mixture was concentrated, filtered and purified by semi-preparative reverse phase HPLC eluting with CH3CN/water (0.1% TFA). (135 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationfiltered
  3. custompurified by semi-preparative reverse phase HPLC
  4. washeluting with CH3CN/water (0.1% TFA)

Sources & evidence

ORD record
ord-20068b3dc6d343e084d32514c5cc4d4c
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

Loading…