Triethylamine → (Pyridin-4-yl)methyl 4-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazine-1-carboxylate

HRID 2062176Notes

Reaction equation

HRID 2062176 reaction equation
[F:1][C:2]1[C:3]([C:9]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:16]3[C:11](=[CH:12][C:13]([CH3:25])=[CH:14][CH:15]=3)[N:10]=2)=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.N1([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)=[O:32])C=CN=C1.C(N(CC)CC)C>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9]1[N:18]=[C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=3)=[O:32])[CH2:21][CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:25])=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 58010890HCID 58010890, compoundHCID 1361214163-Fluoro-2-(7-methyl-4-(piperazin-1-yl)quinazolin-2-yl)phenol

Product 1

HCID 136121401(Pyridin-4-yl)methyl 4-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Fluoro-2-(7-methyl-4-(piperazin-1-yl)quinazolin-2-yl)phenol (50 mg, 0.15 mmol), (pyridin-4-yl)methyl 1H-imidazole-1-carboxylate (53 mg, 0.26 mmol) and triethylamine (30.4 mg, 0.3 mmol) were added into a tube, followed by the addition of DMSO (1 mL). The mixture was stirred at room temperature for 18 h and then filtered, and purified via preparative reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) giving (pyridin-4-yl)methyl 4-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazine-1-carboxylate. LC/MS: m/z 474.30 (M+H)+ at 1.19 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. filtrationfiltered
  2. custompurified via preparative reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Sources & evidence

ORD record
ord-3c7d3fde627e4beeaefa7d915cd7406e
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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