Trifluoroacetic acid → HCID 66712641, compound

HRID 1262447Notes

Reaction equation

HRID 1262447 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH:9]1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=1)=O)(C)(C)C.[CH3:28][O:29][C:30]1[N:35]=[CH:34][C:33]([C:36]2[N:44]3[C:39]([CH:40]=[N:41][C:42](OS(C(F)(F)F)(=O)=O)=[N:43]3)=[CH:38][CH:37]=2)=[CH:32][CH:31]=1.C(O)(C(F)(F)F)=O>>[CH3:28][O:29][C:30]1[N:35]=[CH:34][C:33]([C:36]2[N:44]3[C:39]([CH:40]=[N:41][C:42]([NH:27][C:23]4[CH:24]=[CH:25][CH:26]=[C:21]([CH:9]5[CH2:10][NH:11][CH2:12][CH2:13][NH:8]5)[CH:22]=4)=[N:43]3)=[CH:38][CH:37]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 66712839HCID 66712839, compoundHCID 86661684Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 66712641HCID 66712641, compoundYield 43.2%

Procedure

Analogous to Example 1528d, 2-(3-Amino-phenyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (204 mg, 0.540 mmol) and Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (162 mg, 0.432 mmol) were reacted to afford [7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3-piperazin-2-yl-phenyl)-amine (75 mg, 33%) as the TFA salt. LCMS: 402 (M+H); 1H-NMR (DMSO-d6): 9.74 (s, 1H), 9.5 (br s, 3H), 9.03 (s, 1H), 9.00 (s, 1H), 8.50 (m, 1H), 7.93 (d, 1H, J=8.1 Hz), 7.65 (s, 1H), 7.48 (m, 1H), 7.26 (d, 1H, J=4.8 Hz), 7.19 (d, 1H, J=7.9 Hz), 7.03 (m, 2H), 1.41 (m, 1H), 3.94 (s, 3H), 3.71 (m, 1H), 3.60 (m, 2H), 3.2-3.4 (m, 3H).

Sources & evidence

ORD record
ord-246e85656dd445ba816166351c2c5f1d
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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