N-methyl-2-pyrrolidone → (S)-2-(1-{[2-amino-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol

HRID 2422554Notes

Reaction equation

HRID 2422554 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]1C(=O)CCC1>[OH-].[NH4+]>[NH2:34][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

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 66790522(S)-2-(1-{[2-amino-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

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 (85 mg, 0.18 mmol) in NMP (1 mL) and ammonium hydroxide (15 M, 1 mL) was stirred at 175° C. in a microwave for 10 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 reduced pressure. Purification on silica gel (eluting with ethanol/dichloromethane, 1:9) gave the title compound. MS (+ESI): 445 (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 under reduced pressure
  7. customPurification on silica gel (eluting with ethanol/dichloromethane, 1:9)

Sources & evidence

ORD record
ord-2355d64b09764b52ae1672e8b495629d
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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