Trifluoroacetic acid → HCID 68682443, compound

HRID 1171043Notes

Reaction equation

HRID 1171043 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=[CH:22][C:23](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][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:32][CH:31]=3)[N:12]=2)[CH2:4]1.C([Sn](CCCC)(CCCC)CCCC)C=C.C(C1C=C2C(=CC=1)N=CN=C2)C=C.C(O)(C(F)(F)F)=O>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.CN(C=O)C>[CH2:21]([C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH:28]=[CH:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[CH:32][CH:31]=1)[N:12]=[C:11]2[NH:10][CH2:9][CH:5]1[CH2:6][CH2:7][CH2:8][CH:3]([CH2:2][NH2:1])[CH2:4]1)[CH:22]=[CH2:23]

Participants

9

Reactant 4

HCID 6422Trifluoroacetic acidHCID 90628AllyltributylstannaneHCID 68679474HCID 68679474, compoundHCID 68680837HCID 68680837, compound

Product 1

HCID 68682443HCID 68682443, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Solid supported 6-iodoquinazoline (2) [synthesized according to example 5] (0.054 mmol, 0.54 mmol/g), allyltributyltin (140 mg, 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-allylquinazoline and 2 ml of a mixture of H2O, TFA and dichloromethane (1:49:50) is 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 {6-allyl-2-[2-(4-benzyloxy-phenyl)-vinyl]-quinazolin-4-yl}-(3-aminomethyl-cyclohexylmethyl)-amine;

Workup

  1. customis 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-efd9127cb483437f9ed594e72fff250c
Source dataset
uspto-grants-2010_11
Patent number
US07829566B2

Reaction notes

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