N-methyl-2-pyrrolidone → HCID 66791009, compound

HRID 2422556Notes

Reaction equation

HRID 2422556 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([CH2:19][N:20]3[CH:24]=[C:23]([C:25]([OH:32])([CH2:30][CH3:31])[C:26]([F:29])([F:28])[F:27])[N:22]=[N:21]3)=[CH:7][CH:8]=2)[N:3]=1.C[N:34]1[C:38](=O)[CH2:37][CH2:36][CH2:35]1>N1CCCC1>[F:27][C:26]([F:29])([F:28])[C@:25]([C:23]1[N:22]=[N:21][N:20]([CH2:19][C:6]2[CH:5]=[C:4]3[C:9]([C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[CH:11][C:2]([N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[N:3]3)=[CH:8][CH:7]=2)[CH:24]=1)([OH:32])[CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 250553122-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol

Product 1

HCID 66791009HCID 66791009, compound

Reagents, catalysts & solvents 1

HCID 31268PyrrolidineSolvent

Procedure

A solution of 2-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol (75 mg, 0.16 mmol) in NMP (0.5 mL) and pyrrolidine (0.5 mL) was stirred at 130° C. in a microwave for 20 min. The reaction was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with NH4OH/ethanol/dichloromethane, 1:9:90) gave the title compound. MS (+ESI): 501 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification on silica gel (eluting with NH4OH/ethanol/dichloromethane, 1:9:90)

Sources & evidence

ORD record
ord-621bb3d4f90a404f9e99423195bf3506
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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