1-Methoxy-2-propanol → 2-(4-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-2-fluoro-phenyl}-piperazin-1-yl)-acetamide

HRID 1262389Notes

Reaction equation

HRID 1262389 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.COCC(O)C.[NH2:61][C:62]1[CH:67]=[CH:66][C:65]([N:68]2[CH2:73][CH2:72][N:71]([CH2:74][C:75]([NH2:77])=[O:76])[CH2:70][CH2:69]2)=[C:64]([F:78])[CH:63]=1>>[C:1]([NH:5][S:6]([C:9]1[CH:10]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:61][C:62]4[CH:67]=[CH:66][C:65]([N:68]5[CH2:73][CH2:72][N:71]([CH2:74][C:75]([NH2:77])=[O:76])[CH2:70][CH2:69]5)=[C:64]([F:78])[CH:63]=4)=[N:22]3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 142176Phenyl triflimideHCID 667125502-[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-acetamideHCID 178449976HCID 178449976, compound

Product 1

HCID 667123142-(4-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-2-fluoro-phenyl}-piperazin-1-yl)-acetamide

Procedure

N-tert-Butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (0.092 g, 0.26 mmol), N-Phenylbis(trifluoromethanesulphonimide) (0.112 g, 0.314 mmol), N,N-Diisopropylethylamine (0.139 mL, 0.797 mmol) and 1-Methoxy-2-propanol (4.0 mL, 41 mmol) were combined in a tube and stirred at room temperature for 18 hours. 2-[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-acetamide (0.087 g, 0.34 mmol) was added and the reaction was stirred at room temperature for 4 days to yield an orange solid, 2-(4-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-2-fluoro-phenyl}-piperazin-1-yl)-acetamide; compound with 2 trifluoroacetic acids (35 mg, 16%). LCMS: m/z=581.25 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 9.59 (s, 1H), 8.98 (s, 1H), 8.41 (s, 1H), 8.33 (d, 1H, J=7.9 Hz), 7.95 (s, 1H), 7.80 (d, 1H, J=7.8 Hz), 7.66 (m, 2H), 7.54 (m, 3H), 7.14 (d, 1H, J=4.7 Hz), 7.07 (m, 1H), 6.96 (d, 1H, J=4.7 Hz), 3.95 (s, 2H), 3.5 (m, 2H), 3.31 (m, 4H), 3.09 (m, 2H), 1.05 (s, 9H).

Workup

  1. stirringthe reaction was stirred at room temperature for 4 days

Sources & evidence

ORD record
ord-399b2e0a05b241bd92845e597a420b9e
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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