Dimethylformamide → HCID 68680249, compound

HRID 1171044Notes

Reaction equation

HRID 1171044 reaction equation
NC[CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][NH:10][C:11]2[C:20]3[C:15](=CC=C(C=CC(N(C)C)=O)[CH:19]=3)[N:14]=[C:13]([CH:28]=[CH:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37]C4C=CC=CC=4)=[CH:32][CH:31]=3)[N:12]=2)[CH2:4]1.C[C:45]1[CH:50]=[CH:49][C:48](B(O)O)=[CH:47][CH:46]=1.[CH3:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[CH:62]=[C:63]3C(=CC=2)N=CN=C3)=[CH:57][CH:56]=1.C(O)(C(F)(F)F)=O.[CH3:78][N:79](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClCCl.O>[NH2:79][CH2:78][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][NH:10][C:11]2[C:20]3[C:15](=[CH:63][CH:62]=[C:61]([C:58]4[CH:57]=[CH:56][C:55]([CH3:54])=[CH:60][CH:59]=4)[CH:19]=3)[N:14]=[C:13]([CH:28]=[CH:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[CH:32][CH:31]=3)[N:12]=2)[CH2:4]1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 79799Tolylboronic acidHCID 68680238HCID 68680238, compoundHCID 68680837HCID 68680837, compound

Product 1

HCID 68680249HCID 68680249, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Solid supported 6-iodoquinazoline (2) [synthesized according to example 5] (0.054 mmol, 0.54 mmol/g), 4-methylphenylboronic acid (0.5 mmol), Pd(PPh3)4 (20 mg), and 2 ml DMF are placed in a fritted polypropylene tube. The mixture is agitated at 80° got 24 h. After cooling to rt, the mixture is customary worked up for solid phase reactions. The solid supported 6-(4-methylphenyl)quinazoline and 2 ml of a mixture of H2O, TFA and dichloromethane (1:49:50) are placed in a fritted polypropylene tube. The contents are shaken for 2 h at rt. The suspension is filtered and the resin is washed with dichloromethane (1 ml) and methanol (1 ml) respectively. Evaporation of the combined filtrates give (3-aminomethyl-cyclohexylmethyl)-{2-[2-(4-benzyloxy-phenyl)-vinyl]-6-4-tolyl-quinazolin-4-yl}-amine;

Workup

  1. customare placed in a fritted polypropylene tube
  2. stirringThe contents are shaken for 2 h at rt
  3. filtrationThe suspension is filtered
  4. washthe resin is washed with dichloromethane (1 ml) and methanol (1 ml) respectively
  5. customEvaporation of the combined filtrates

Sources & evidence

ORD record
ord-edb61d34b3704a0d9ed2990ddf433577
Source dataset
uspto-grants-2010_11
Patent number
US07829566B2

Reaction notes

Loading…