Trifluoroacetic acid → 2-(4-Amino-pyrrolo[2,1-f][1,2,4]triazin-7-ylmethyl)-cyclopropanecarboxylic acid ethyl ester

HRID 1972875Notes

Reaction equation

HRID 1972875 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[CH:9]([C:11]1[N:19]2[C:14]([C:15]([NH2:20])=[N:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1)O)=[O:5])[CH3:2].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[CH2:9][C:11]1[N:19]2[C:14]([C:15]([NH2:20])=[N:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 585294272-[(4-Amino-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-hydroxy-methyl]-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 585296522-(4-Amino-pyrrolo[2,1-f][1,2,4]triazin-7-ylmethyl)-cyclopropanecarboxylic acid ethyl esterYield 26.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[(4-amino-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-hydroxy-methyl]-cyclopropanecarboxylic acid ethyl ester (1.75 g, 6.3 mmol) in dichloromethane (17.5 mL) was added dropwise into a mixture of triethylsilane (3 g, 25 mmol) and TFA (17.5 mL) in ice water bath. It was stirred at rt for overnight. 2N sodium carbonate solution (10 mL) was added and organic layer was separated, dried and concentrated. The residue was purified by Biotage® to give desired product 0.43 g (26). 1H NMR (300 MHz, DMSO-d6) δ 8.80 (s, 1 H), 8.75 (bs, 2 H), 6.80 (s, 1 H), 6.60 (m, 1 H), 4.0 (m, 2 H), 2.9 (d, 2 H), 1.5 (m, 2 H), 1.2 (t, 3 H), 1.0 (m, 2 H); ES-MS m/z 261.07 [M+H]+, HPLC RT (min) 2.03.

Workup

  1. customorganic layer was separated
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by Biotage®

Sources & evidence

ORD record
ord-8b59af8ab3394996b16cb8ed1b0acaf5
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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