5,6-Dimethylbenzimidazole → HCID 67298169, compound

HRID 1520351Notes

Reaction equation

HRID 1520351 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([NH2:14])=[O:13])[CH:10]=2)[NH:5][C:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:3]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:48][C:49]1[C:57]([CH3:58])=[CH:56][C:52]2[NH:53][CH:54]=[N:55][C:51]=2[CH:50]=1>CN(C=O)C>[CH3:48][C:49]1[C:57]([CH3:58])=[CH:56][C:52]2[N:53]([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([C:12]([NH2:14])=[O:13])[CH:10]=4)[N:5]=[C:4]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[N:3]=3)[CH:54]=[N:55][C:51]=2[CH:50]=1

Participants

5

Reactant 3

HCID 6755,6-DimethylbenzimidazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178513582HCID 178513582, compound

Product 1

HCID 67298169HCID 67298169, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-oxo-2-(pyridin-3-yl)-1,4-dihydroquinazoline-6-carboxamide (prepared as described in scheme 4) (100 mg, 0.376 mmol, 1.0 eq.) in dry DMF (20 mL) was added benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (216 mg, 0.488 mmol, 1.3 eq.) and diaza(1,3)bicyclo[5.4.0]undecene (114.5 mg, 0.752 mmol, 2.0 eq.) following a procedure outlined in J. Org. Chem., 2007, 72, 1019440210. To the clear solution was then added 5,6-dimethyl-1H-benzo[d]imidazole (165.2 mg, 1.13 mmol, 3.0 eq.) and the mixture was stirred overnight at room temperature. The resultant precipitate was then collected by filtration and washed with dichloromethane, water, and ether. The product was dried in vacuo to give 26.3 mg of the desired product: (xlviii-a) as an off-white solid (6.7%). LCMS m/z=395.1 (M+1) (Method C) (retention time=1.68 min). 1H NMR (300 MHz, DMSO) δ 9.69 (s, 1H), 8.90 (s, 1H), 8.82 (d, J=15.2 Hz, 2H), 8.66 (s, 1H), 8.54 (d, j=8.6 Hz, 1H), 8.42 (s, 1H), 8.30 (d, J=8.5 Hz, 1H), 7.79 (s, 1H), 7.68 (s, 3H), 2.39 (s, 3H), 2.36 (s, 3H).

Workup

  1. filtrationThe resultant precipitate was then collected by filtration
  2. washwashed with dichloromethane, water, and ether
  3. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-a5ae9a604ac64bae8da7a2bbd6b8f8cd
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

Loading…