Trifluoroacetic acid → {1-[4-(3-Chloro-4-hydroxy-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl]-piperidin-4-yl}-carbamic acid, tert-butyl ester

HRID 1829935Notes

Reaction equation

HRID 1829935 reaction equation
[Br-].Cl[C:3]1[C:8]2=[C:9]([CH2:12][N+:13]([CH2:18][CH3:19])([CH2:16][CH3:17])CC)[CH:10]=[CH:11][N:7]2[N:6]=[CH:5][N:4]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([Cl:28])[CH:22]=1.[C:29]([O:33][C:34](=[O:42])[NH:35][CH:36]1CCNCC1)([CH3:32])([CH3:31])[CH3:30].FC(F)(F)C(O)=O>C(#N)C.CO>[Cl:28][C:23]1[CH:22]=[C:21]([NH:20][C:3]2[C:8]3=[C:9]([CH2:12][N:13]4[CH2:16][CH2:17][CH:36]([NH:35][C:34](=[O:42])[O:33][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:19][CH2:18]4)[CH:10]=[CH:11][N:7]3[N:6]=[CH:5][N:4]=2)[CH:26]=[CH:25][C:24]=1[OH:27]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 775784-Amino-2-chlorophenolHCID 7238334-(N-Boc-amino)piperidineHCID 11544775(4-Chloro-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl)-triethyl-ammonium bromide

Product 1

HCID 21031521{1-[4-(3-Chloro-4-hydroxy-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl]-piperidin-4-yl}-carbamic acid, tert-butyl esterYield 73.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 21A (2.5 g) was prepared from 1E (2.5 g, 7.2 mmol), 4-amino-2-chlorophenol (1.03 g, 7.2 mmol) and piperidine-4-yl-carbamic acid tert-butyl ester (1.44 g, 7.2 mmol) in acetonitrile by a route analogous to that used in Method Two for the preparation of 1F. Analytical HPLC retention time=2.436 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=473+.

Sources & evidence

ORD record
ord-804d44cd3f5842aea5dd0c5356e18b35
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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