Dimethylformamide → N-tert-Butyl-3-{2-[4-(4-morpholin-4-yl-cyclohexyl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzenesulfonamide

HRID 1262090Notes

Reaction equation

HRID 1262090 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C.CN(C)C=O.[N:60]1([CH:66]2[CH2:71][CH2:70][CH:69]([C:72]3[CH:77]=[CH:76][C:75]([NH2:78])=[CH:74][CH:73]=3)[CH2:68][CH2:67]2)[CH2:65][CH2:64][O:63][CH2:62][CH2:61]1>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:78][C:75]4[CH:76]=[CH:77][C:72]([CH:69]5[CH2:68][CH2:67][CH:66]([N:60]6[CH2:61][CH2:62][O:63][CH2:64][CH2:65]6)[CH2:71][CH2:70]5)=[CH:73][CH:74]=4)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 142176Phenyl triflimideHCID 590114594-[4-(4-morpholinyl)cyclohexyl]BenzenamineHCID 178449976HCID 178449976, compound

Product 1

HCID 66711231N-tert-Butyl-3-{2-[4-(4-morpholin-4-yl-cyclohexyl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzenesulfonamide

Procedure

The title compound was prepared in the following manner: N-tert-Butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (70 mg, 0.2 mmol), N-Phenylbis(trifluoromethanesulphonimide) (82.6 mg, 0.231 mmol), N,N-Diisopropylethylamine (0.11 mL, 0.62 mmol), and N,N-Dimethylformamide (2 mL, 20 mmol) and stir at room temperature for half an hour. Added 4-(4-Morpholin-4-yl-cyclohexyl)-phenylamine (280 mg, 1.1 mmol) and stir at 80° C. overnight. The mixture was concentrated and purified using the gilson. The most pure fractions were combined basified with sat. sodium bicarbonate and extracted with DCM, dried filtered and concentrated to give a yellow solid (30 mg, 20%). MP 160-163 C. LCMS (E/I+) 589 (M+H). NMR 1H (DMSO-d6)-9.44 (s, 1H), 9.02 (s, 1H), 8.57 (s, 1H), 8.33-8.40 (m, 1H), 7.86 (d, 1H, J=8.03), 7.59-7.76 (m, 3H), 7.18-7.24 (m, 2H), 6.98 (d, 1H, J=4.8 Hz), 3.60-3.64 (m, 2H), 3.55-3.59 (m, 1H), 2.55-2.64 (m, 1H), 2.49-2.51 (m, 4H), 2.36-2.42 (m, 2H), 2.14-2.19 (m, 1H), 1.89-1.98 (m, 2H), 1.78-1.88 (m, 2H), 1.44-1.54 (m, 4H), 1.11 (s, 9H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified
  3. extractionextracted with DCM
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5bb2a80e60364a42bcbad0b6fbbecb59
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…