N-[4-(Trimethylstannyl)-2-pyrimidinyl]acetamide → N-(4-(3-(2-(2-Fluorophenyl)-3-methylquinolin-4-ylamino)-4-morpholinophenyl)pyrimidin-2-yl)acetamide

HRID 1431293Notes

Reaction equation

HRID 1431293 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[C:6]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:10]=2[CH3:26])[CH:7]=1.C[Sn](C)(C)[C:35]1[CH:40]=[CH:39][N:38]=[C:37]([NH:41][C:42](=[O:44])[CH3:43])[N:36]=1>C1(C)C=CC=CC=1.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>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:11]1[C:10]([CH3:26])=[C:9]([NH:8][C:6]2[CH:7]=[C:2]([C:35]3[CH:40]=[CH:39][N:38]=[C:37]([NH:41][C:42](=[O:44])[CH3:43])[N:36]=3)[CH:3]=[CH:4][C:5]=2[N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

5

Reactant 2

HCID 11483414N-[4-(Trimethylstannyl)-2-pyrimidinyl]acetamideHCID 59631162N-(5-Bromo-2-morpholinophenyl)-2-(2-fluorophenyl)-3-methylquinolin-4-amine

Product 1

HCID 67508373N-(4-(3-(2-(2-Fluorophenyl)-3-methylquinolin-4-ylamino)-4-morpholinophenyl)pyrimidin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of N-(5-bromo-2-morpholinophenyl)-2-(2-fluorophenyl)-3-methylquinolin-4-amine (100 mg, 203 μmol), N-(4-(trimethylstannyl)pyrimidin-2-yl)-acetamide (91 mg, 305 μmol) and tetrakis(triphenylphosphine)palladium(0) (23 mg, 20 μmol) in toluene (4.00 mL) was purged with nitrogen and heated to gentle reflux. After 3.5 h LC-MS indicated no starting bromide remained and the reaction was removed from heat and left stirring overnight at rt before concentrating under reduced pressure. The concentrate was dissolved in 3 mL DMF and purified by reversed-phase HPLC. Mass Spectrum (ESI) m/e=549.3 (M+1).

Workup

  1. customwas purged with nitrogen
  2. temperatureheated to gentle reflux
  3. customthe reaction was removed
  4. temperaturefrom heat
  5. waitleft
  6. concentrationbefore concentrating under reduced pressure
  7. dissolutionThe concentrate was dissolved in 3 mL DMF
  8. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-c0acc4a78a6a459b9f65c7b7e18d7de2
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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