Trifluoroacetic acid → [5-(4-Amino-piperidin-1-ylmethyl)-pyrrolo[2,1-f][1,2,4]triazin-4-yl]-[3-chloro-4-(pyridin-4-ylmethoxy)-phenyl]-amine

HRID 1829937Notes

Reaction equation

HRID 1829937 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:22]3=[C:23]([CH2:26][N:27]4[CH2:32][CH2:31][CH:30]([NH:33]C(=O)OC(C)(C)C)[CH2:29][CH2:28]4)[CH:24]=[CH:25][N:21]3[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.NC1CCN(CC2C=CN3C=2C(NC2C=CC(OCC4C=CC=CN=4)=C(Cl)C=2)=NC=N3)CC1.FC(F)(F)C(O)=O>CO>[NH2:33][CH:30]1[CH2:31][CH2:32][N:27]([CH2:26][C:23]2[CH:24]=[CH:25][N:21]3[C:22]=2[C:17]([NH:16][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]4[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=4)=[C:2]([Cl:1])[CH:3]=2)=[N:18][CH:19]=[N:20]3)[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 111787565-((4-aminopiperidin-1-yl)methyl)-N-(3-chloro-4-(pyridin-2-ylmethoxy)phenyl)pyrrolo[1,2-f][1,2,4]triazin-4-amineHCID 21031526(1-{4-[3-Chloro-4-(pyridin-4-ylmethoxy)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl}-piperidin-4-yl)-carbamic acid, tert-butyl ester

Product 1

HCID 22055288[5-(4-Amino-piperidin-1-ylmethyl)-pyrrolo[2,1-f][1,2,4]triazin-4-yl]-[3-chloro-4-(pyridin-4-ylmethoxy)-phenyl]-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 21C (31 mg) was prepared from 21B by a route analogous to that used for the preparation of 1G as a white solid. Analytical HPLC retention time=1.480 min. (Chromolith Speed ROD column 4.6×50 mm, 10–90% aqueous methanol over 4 minutes containing 0.2% trifluoroacetic acid, 4 mL/min, monitoring at 254 nm) and a LC/MS M++1=464+.

Sources & evidence

ORD record
ord-70b15bd8d41c498e81cc60beb5d3fe52
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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