6-(Morpholino)pyridin-3-amine → [7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-amine

HRID 1261895Notes

Reaction equation

HRID 1261895 reaction equation
N1(C2N=CC(N)=CC=2)CCOCC1.CN1CCN(CCOC2C=CC(N)=CC=2)CC1.FC(F)(F)C(O)=O.[CH3:38][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]1[N:54]2[C:49]([CH:50]=[N:51][C:52]([NH:55][C:56]3[CH:61]=[CH:60][C:59]([O:62][CH2:63][CH2:64][N:65]4[CH2:70][CH2:69][N:68]([CH3:71])[CH2:67][CH2:66]4)=[CH:58][CH:57]=3)=[N:53]2)=[CH:48][CH:47]=1>>[CH3:38][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]1[N:54]2[C:49]([CH:50]=[N:51][C:52]([NH:55][C:56]3[CH:57]=[CH:58][C:59]([O:62][CH2:63][CH2:64][N:65]4[CH2:66][CH2:67][N:68]([CH3:71])[CH2:69][CH2:70]4)=[CH:60][CH:61]=3)=[N:53]2)=[CH:48][CH:47]=1

Participants

4

Reactant 3

HCID 1040596-(Morpholino)pyridin-3-amineHCID 230087924-[2-(4-Methylpiperazin-1-yl)ethoxy]anilineHCID 866616637-(2-methoxyphenyl)-N-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]pyrrolo[2,1-f][1,2,4]triazin-2-amine;2,2,2-trifluoroacetic acid

Product 1

HCID 66710733[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-amine

Procedure

The titled compound was prepared in an analogous fashion to Example 47 replacing 6-Morpholin-4-yl-pyridin-3-ylamine with 4-[2-(4-Methyl-piperazin-1-yl)-ethoxy]-phenylamine to [7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-amine; compound with trifluoro-acetic acid as a yellow powder. LCMS (E/I+) 459.9 (M+H). NMR 1H (DSMO-d6)-9.27 (s, 1H), 8.93 (s, 1H7.81 (dd, 1H, Jj=1.40, 6.17 Hz), 7.65 (d, 2H, J=9.00 Hz), 7.45 (t, 1H, J=9.72 Hz), 7.21 (d, 1H, J=8.32 Hz), 7.12 (t, 1H, J=7.49 Hz), 6.94 (d, 1H, J=4.61 hz), 6.91 (d, 1H, J=4.64), 6.84 (d, 2H, J=9.00 Hz), 4.19 (t, 2H, J=4.72 Hz), 3.78 (s, 3H), 2.90-3.70 (bm, 10), 2.84 (s, 3H).

Sources & evidence

ORD record
ord-08b9c9ae4f884aa29db0709f2cdc6e8a
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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