Ytterbium triflate → HCID 50897818, compound

HRID 1500602Notes

Reaction equation

HRID 1500602 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:23][CH3:24])=[C:7]([CH:22]=1)[CH2:8][O:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([NH:17][C:18](=[O:20])[CH3:19])=[CH:12][C:11]=1[CH3:21])=O.[NH2:25][C:26]1[CH:41]=[CH:40][CH:39]=[CH:38][C:27]=1[C:28]([NH:30][CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)=[O:29].C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>CCO>[CH3:24][O:23][C:6]1[CH:5]=[CH:4][C:3]([CH:1]2[N:30]([CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[C:28](=[O:29])[C:27]3[C:26](=[CH:41][CH:40]=[CH:39][CH:38]=3)[NH:25]2)=[CH:22][C:7]=1[CH2:8][O:9][C:10]1[C:11]([CH3:21])=[CH:12][C:13]([NH:17][C:18](=[O:20])[CH3:19])=[CH:14][C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 2733225Ytterbium triflateHCID 28031922-amino-N-(pyridin-3-ylmethyl)benzamideHCID 86674670HCID 86674670, compound

Product 1

HCID 50897818HCID 50897818, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-(5-formyl-2-methoxybenzyloxy)-3,5-dimethylphenyl)acetamide (100 mg, 0.305 mmol), 2-amino-N-(pyridin-3-ylmethyl)benzamide (83 mg, 0.367 mmol), and 0.2 equiv of Yb(OTf)3 in 5 mL of EtOH were heated at 80° C. for 4 h. The reaction mixture was concentrated under reduced pressure and the residue was chromatographed on silica-gel using 2-40% Methanol in DCM to give the desired product N-(4-(2-methoxy-5-(4-oxo-3-(pyridin-3-ylmethyl)-1,2,3,4-tetrahydroquinazolin-2-yl)benzyloxy)-3,5-dimethylphenyl)acetamide (68.2 mg, 0.127 mmol, 41.6% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.96 (s, 3 H), 2.08 (s, 6 H), 3.74 (s, 3 H), 3.98 (d, J=15.7 Hz, 1 H), 4.61 (s, 2 H), 5.07 (d, J=15.3 Hz, 1 H), 5.82 (d, J=2.3 Hz, 1 H), 6.58-6.74 (m, 2 H), 6.97 (d, J=8.2 Hz, 1 H), 7.12-7.37 (m, 6 H), 7.46 (d, J=2.0 Hz, 1 H), 7.64 (t, J=6.8 Hz, 2 H), 8.35-8.47 (m, 2 H), 9.67 (s, 1 H); LC/MS (electrospray+ve), m/z 537.2 (MH)+, Retention time t=4.23 min; Purity: UV220>98%, UV254>98%; HRMS (ESI): m/z calcd for C32H32N4O4 [M+H]+537.2511, found 537.2511.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was chromatographed on silica-gel

Sources & evidence

ORD record
ord-85ea3844552746899e0252b0efbe1ba3
Source dataset
uspto-grants-2015_12
Patent number
US09206154B2

Reaction notes

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