Toluene → HCID 89783740, compound

HRID 1056430Notes

Reaction equation

HRID 1056430 reaction equation
[NH2:1][C:2]1[C:16]([Br:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)=[O:5].[C:18](=O)(OC(Cl)(Cl)Cl)[O:19]C(Cl)(Cl)Cl.C(N(CC)CC)C.C1(C)C=CC=CC=1>C(Cl)Cl>[Br:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:3]2[C:2]=1[NH:1][C:18](=[O:19])[N:6]([CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)[C:4]2=[O:5]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 94429Triphosgene2×HCID 89781888HCID 89781888, compound

Product 1

HCID 89783740HCID 89783740, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-amino-3-bromo-N-(tetrahydro-2H-pyran-4-yl)benzamide (515a, 1.54 g, 5.15 mmol), bis(trichloromethyl) carbonate (0.764 g, 2.57 mmol), and triethylamine (3.59 mL, 25.7 mmol) in DCM (51.5 mL) was refluxed for 16 h. Toluene (50 mL) was added to the clear solution; this mixture was partially concentrated to remove the DCM. More bis(trichloromethyl) carbonate (0.764 g, 2.57 mmol) was added, and the yellow solution was heated to 90° C. for 1 h. The reaction mixture was concentrated to give 8-bromo-3-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione (515b) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.56-1.62 (m, 2H) 2.87 (qd, J=12.39, 4.69 Hz, 2H) 3.52 (td, J=12.03, 1.76 Hz, 2H) 4.10 (dd, J=11.54, 4.69 Hz, 2H) 5.11 (tt, J=12.18, 3.96 Hz, 1H) 7.11 (t, J=8.02 Hz, 1H) 7.79 (dd, J=7.82, 1.17 Hz, 1H) 8.09 (s, 1H) 8.11 (s, 1H). MS (ESI, pos. ion) m/z: 325.0/326.9 (M+1).

Workup

  1. concentrationthis mixture was partially concentrated
  2. customto remove the DCM
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d32335514a834c179f913e86bf33a6ae
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…