Ytterbium triflate → HCID 50897771, compound

HRID 1500603Notes

Reaction equation

HRID 1500603 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][O:9][CH3:10])=[O:5].[CH:15]([C:17]1[CH:18]=[CH:19][C:20]([O:37][CH3:38])=[C:21]([CH:36]=1)[CH2:22][O:23][C:24]1[C:29]([CH3:30])=[CH:28][C:27]([NH:31][C:32](=[O:34])[CH3:33])=[CH:26][C:25]=1[CH3:35])=O.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>[CH3:38][O:37][C:20]1[CH:19]=[CH:18][C:17]([CH:15]2[N:6]([CH2:7][CH2:8][O:9][CH3:10])[C:4](=[O:5])[C:3]3[C:2](=[CH:14][CH:13]=[CH:12][CH:11]=3)[NH:1]2)=[CH:36][C:21]=1[CH2:22][O:23][C:24]1[C:25]([CH3:35])=[CH:26][C:27]([NH:31][C:32](=[O:34])[CH3:33])=[CH:28][C:29]=1[CH3:30]

Participants

5

Reactant 3

HCID 2733225Ytterbium triflateHCID 159430542-Amino-N-(2-methoxyethyl)benzamideHCID 86674670HCID 86674670, compound

Product 1

HCID 50897771HCID 50897771, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-amino-N-(2-methoxyethyl)benzamide (71.2 mg, 0.367 mmol), N-(4-(5-formyl-2-methoxybenzyloxy)-3,5-dimethylphenyl)acetamide (100 mg, 0.305 mmol) and 0.2 equiv of Yb(OTf)3 in 5 mL of EtOH were heated at 80° C. for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was chromatographed on silica-gel using 10-80% ethyl acetate in DCM to give the N-(4-(2-methoxy-5-(3-(2-methoxyethyl)-4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)benzyloxy)-3,5-dimethylphenyl)acetamide (77.9 mg, 0.155 mmol, 50.6% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.97 (s, 3 H), 2.09 (s, 6 H), 2.90 (ddd, J=13.5, 6.7, 6.5 Hz, 1 H), 3.19 (s, 3 H), 3.31-3.53 (m, 2 H), 3.74 (s, 3 H), 3.86-4.06 (m, 1 H), 4.63 (s, 2 H), 5.85 (d, J=2.3 Hz, 1 H), 6.53-6.69 (m, 2 H), 6.98 (d, J=8.6 Hz, 1 H), 7.12-7.22 (m, 3 H), 7.22-7.31 (m, 2 H), 7.47 (d, J=2.3 Hz, 1 H), 7.61 (d, J=6.7 Hz, 1 H), 9.67 (s, 1 H); LC/MS (electrospray+ve), m/z 504.2 (MH)+, Retention time t=5.27 min; Purity: UV220>98%, UV254>98%; HRMS (ESI): m/z calcd for C29H33N3O5 [M+H]+504.2496, found 504.2498.

Workup

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

Sources & evidence

ORD record
ord-6ca2504b0cd64c93a108ca67532780b1
Source dataset
uspto-grants-2015_12
Patent number
US09206154B2

Reaction notes

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