Trifluoroacetic acid → HCID 58529315, compound

HRID 1972971Notes

Reaction equation

HRID 1972971 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:25]3[CH:26]=[CH:27][C:28]4[C:32]([CH:33]=3)=[N:31][N:30]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]=4[NH2:41])[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17](=[O:24])[CH2:18][N:19](C)[C:20](=O)O)[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O.CCOC(C)=O>C(Cl)Cl>[NH2:1][C:2]1[C:7]2=[C:8]([C:25]3[CH:26]=[CH:27][C:28]4[C:32]([CH:33]=3)=[N:31][N:30]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]=4[NH2:41])[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17](=[O:24])[CH2:18][NH:19][CH3:20])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 86659606HCID 86659606, compound

Product 1

HCID 58529315HCID 58529315, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (2-(4-[4-Amino-5-(3-amino-2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-piperidin-1-yl)-2-oxo-ethyl)-methyl-carbamic acid tart-butyl ester (30 mg, 0.049 mmol) in anhydrous DCM (1.0 mL) was added trifluoroacetic acid (1.0 mL), and the reaction mixture was stirred at rt. After 1 h, the mixture was poured into EtOAc (75 mL), and the organic phase was washed with aqueous, saturated NaHCO3 solution (3×25 mL), water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Trituration with DCM-hexane afforded the title compound (24.7 mg, 98.5%) as a pink solid. 1H NMR (300 MHz, DMSO-d6) δ 7.88 (s, 1H), 7.71 (d, 1H), 7.34 to 7.29 (m, 2H), 7.27 to 7.21 (m, 3H), 7.15 (s, 1H), 6.73 (dd, 1H), 6.54 (s, 1H), 6.37 (broad s, 2H), 5.38 (s, 2H), 4.50 (d, 1H), 3.90 (d, 1H), 3.42 to 3.27 (m, 3H), 3.13 (t, 1H), 2.76 to 2.66 (m, 1H), 2.26 (s, 3H), 2.05 to 1.99 (m, 3H), 1.68 to 1.49 (m, 2H); ES-MS m/z 510.1 [M+H]+, RT (min) 1.56.

Workup

  1. washthe organic phase was washed with aqueous, saturated NaHCO3 solution (3×25 mL), water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64fb6590d10949b6acaf6560136a23b3
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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