Triethylamine → methyl (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-[4-(6-hydroxy-2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-4-oxo-butanoate

HRID 643149

Reaction equation

HRID 643149 reaction equation
[NH2:1][C:2]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:5]([CH2:6][C@@H:7]([CH2:12][C:13]([O-:15])=O)[C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=1[Cl:22].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[OH:52][C:53]1[CH:54]=[C:55]2[C:60](=[CH:61][CH:62]=1)[NH:59][C:58](=[O:63])[N:57]([CH:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1)[CH2:56]2.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:5]([CH2:6][C@@H:7]([CH2:12][C:13]([N:67]2[CH2:66][CH2:65][CH:64]([N:57]3[CH2:56][C:55]4[C:60](=[CH:61][CH:62]=[C:53]([OH:52])[CH:54]=4)[NH:59][C:58]3=[O:63])[CH2:69][CH2:68]2)=[O:15])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=1[Cl:22]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 211022076-Hydroxy-3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-oneHCID 866042951-methyl (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-succinate

Product 1

HCID 69071695methyl (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-[4-(6-hydroxy-2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-4-oxo-butanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.37 g (4.04 mmol) 1-methyl (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-succinate, 1.42 g (4.40 mmol) TBTU, 0.63 mL (4.50 mmol) triethylamine and 1.00 g (4.04 mmol) 6-hydroxy-3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one in 10 mL DMF was stirred for 3 h at RT. The reaction mixture was poured onto 300 mL saturated NaHCO3 solution, the precipitated substance was suction filtered, washed with 50 mL water and dried at 60° C. in the circulating air dryer.

Workup

  1. filtrationfiltered
  2. washwashed with 50 mL water
  3. customdried at 60° C. in the circulating air dryer

Sources & evidence

ORD record
ord-42f657904f034372909ef82d7e496329
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Linked notes

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