Dimethylformamide → HCID 68679805, compound

HRID 1171045Notes

Reaction equation

HRID 1171045 reaction equation
BrC1C=CC=CC=1C=CC1[N:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)N=1.C1(B(O)O)C=CC=CC=1.[C:29]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:34]=[CH:33][C:32]([CH:35]=[CH:36][C:37]2[N:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=2)=[CH:31][CH:30]=1.C(O)(C(F)(F)F)=O.[CH3:60][N:61](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.C(N(CC)CC)C>[NH2:15][CH2:14][CH:13]1[CH2:8][CH2:9][CH2:10][CH:11]([CH2:60][NH:61][C:45]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=[C:37]([CH:36]=[CH:35][C:32]3[CH:31]=[CH:30][C:29]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[CH:34][CH:33]=3)[N:46]=2)[CH2:12]1

Participants

10

Reactant 5

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 66827Phenylboronic AcidHCID 68680887HCID 68680887, compoundHCID 68682180HCID 68682180, compound

Product 1

HCID 68679805HCID 68679805, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

The solid supported 2-bromostyrylquinazoline (3) (0.054 mmol, 0.54 mmol/g), phenylboronic acid (0.5 mmol), Pd(PPh3)4 (20 mg), triethylamine (20 ml) and 2 ml DMF are placed in a fritted polypropylene tube. The mixture is agitated at 80° for 24 h. After cooling to rt, the mixture is customary worked up for solid phase reactions. The solid-supported 2-(2-biphenyl-4-yl-vinyl)-quinazoline 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 (3-aminomethyl-cyclohexylmethyl)-[2-(2-biphenyl-4-yl-vinyl)-quinazolin-4-yl]-amine;

Workup

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

Sources & evidence

ORD record
ord-74c542bbef2e4fd9b35c0867bb1d6dd6
Source dataset
uspto-grants-2010_11
Patent number
US07829566B2

Reaction notes

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