Binap, (A+-)- → N,N-dimethyl-1-{3-[(3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)amino]phenyl}methanesulfonamide

HRID 2374964Notes

Reaction equation

HRID 2374964 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14]([NH:17][C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)=[N:15]3)=[C:10]([CH3:30])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:31][C:32]1[CH:33]=[C:34]([CH2:38][S:39]([N:42]([CH3:44])[CH3:43])(=[O:41])=[O:40])[CH:35]=[CH:36][CH:37]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>O1CCOCC1>[CH3:43][N:42]([CH3:44])[S:39]([CH2:38][C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([NH:31][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[N:16]4[C:11]([CH:12]=[N:13][C:14]([NH:17][C:18]5[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=5)=[N:15]4)=[C:10]([CH3:30])[N:9]=3)[CH:3]=2)[CH:33]=1)(=[O:40])=[O:41]

Participants

6

Reactant 4

HCID 634876Binap, (A+-)-HCID 112135557-(3-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amineHCID 23676156Sodium t-butoxideHCID 432562151-(3-aminophenyl)-N,N-dimethylmethanesulfonamide

Product 1

HCID 58711956N,N-dimethyl-1-{3-[(3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)amino]phenyl}methanesulfonamideYield 24.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

In a similar manner as described in Example 66, 7-(3-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (Example 9) (40 mg, 0.085 mmol), 1-(3-aminophenyl)-N,N-dimethylmethanesulfonamide (21.9 mg, 0.102 mmol), (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl ((S)-BINAP) (15.9 mg, 0.026 mmol), Tris(dibenzylidineacetone)dipalladium (0) (7.8 mg, 0.008 mmol) and sodium t-butoxide (11.4 mg, 0.12 mmol) in 1,4-dioxane (1.5 mL) were heated with microwave radiation at 140° C. for 60 minutes in a sealed reaction vessel to give N,N-dimethyl-1-{3-[(3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)amino]phenyl}methanesulfonamide (0.0125 g) as a yellow solid. 1H NMR (CDCl3) δ8.80 (s, 1H), 8.15 (dd, J=1.8, 1.8 Hz, 1H), 8.06-8.04 (m, 1H), 7.36 (dd, J=8.0, 7.9 Hz, 1H), 7.25-7.22 (m, 2H), 7.16 (dd, J=1.9, 1.8, 1H), 7.10 (ddd, J=8.1, 2.4, 0.9 Hz, 1H), 6.93-6.91 (m, 4H), 6.10 (s, 1H), 4.17 (s, 2H), 3.84-3.83 (m, 9H) 2.76 (s, 6H), 2.60 (s, 3H). MS m/z 605 (M+1).

Sources & evidence

ORD record
ord-cff713f23281468cb80fe267e097d72f
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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