HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Acetic Acid → Methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate

HRID 2104514
Notes
Print preview

Reaction equation

HRID 2104514 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.[CH3:30][O:31][C:32](=[O:42])[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]=O)=[CH:36][CH:35]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C1COCC1>[C:22]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[C:4]1[CH:3]=[C:2]([NH:1][CH2:40][C:37]3[CH:36]=[CH:35][C:34]([CH2:33][C:32]([O:31][CH3:30])=[O:42])=[CH:39][CH:38]=3)[CH:7]=[CH:6][CH:5]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:19])[F:20])(=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 11326798[4-(3-Aminophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)MethanoneHCID 19363032Methyl 2-(4-formylphenyl)acetate

Product 1

HCID 16718795Methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetateYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

[4-(3-Aminophenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (0.39 g, 1.0 mmol) and (4-formyl-phenyl)-acetic acid methyl ester (0.17 g, 0.96 mmol) were mixed in THF (15 mL) and then treated with NaBH(OAc)3 (0.43 g, 2.0 mml) and acetic acid (0.5 mL). After stirring at 40° C. under a N2 atmosphere for 2 h the mixture was quenched with water and then extracted with ethyl acetate. The organic residue was purified by silica gel chromatography using 5-50% EtOAc/hexanes as eluent to provide methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate as an orange solid (0.30 g, 54%): MS (EI) m/z 555.3 (M+H)+; 1H NMR (DMSO-d6): δ 3.61 (s, 3H), 3.66 (s, 2H), 4.12 (d, J=6.0 Hz, 2H), 6.40 (d, J=6.8 Hz, 2H), 6.49 (d, J=6.8 Hz, 2H), 6.98 (t, J=7.7 Hz, 1H), 7.18-7.22 (m, 4H), 7.36 (t, J=7.5 Hz, 2H), 7.55 (t, J=7.4 Hz, 1H), 7.59 (d, J=9.0 Hz, 2H), 7.72 (t, J=8.6 Hz, 1H), 7.99 (d, J=8.5 Hz, 1H), 8.30 (d, J=7.3 Hz, 1H), 9.08 (s, 1H).

Workup

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-db468764b3d0410690623b753dcec760
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576215B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes