HCID 68467005, compound → HCID 44626360, compound

HRID 506196Notes

Reaction equation

HRID 506196 reaction equation
[C:1]([C:3]1[C:4]([NH:32][C:33]2[C:34]([CH3:42])=[C:35]3[C:39](=[CH:40][CH:41]=2)[NH:38][CH:37]=[CH:36]3)=[C:5]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][C:15]([CH2:18][N:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)=[CH:14][C:12]=3[CH:13]=2)[CH:6]=[N:7][CH:8]=1)#[N:2]>FC(F)(F)C(O)=O.C(Cl)Cl>[CH3:42][C:34]1[C:33]([NH:32][C:4]2[C:3]([C:1]#[N:2])=[CH:8][N:7]=[CH:6][C:5]=2[C:9]2[O:10][C:11]3[CH:17]=[CH:16][C:15]([CH2:18][N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[CH:14][C:12]=3[CH:13]=2)=[CH:41][CH:40]=[C:39]2[C:35]=1[CH:36]=[CH:37][NH:38]2

Participants

3

Reactant 1

HCID 68467005HCID 68467005, compound

Product 1

HCID 44626360HCID 44626360, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A mixture of tert-butyl 4-[(2-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}-1-benzofuran-5-yl)methyl]piperazine-1-carboxylate (63 mg, 0.11 mmol) in 10% trifluoroacetic acid/CH2Cl2 was stirred at room temperature for 4 h, concentrated in vacuo, and the residue was purified by preparative HPLC (column: Prodigy ODS3, 4.6×150 mm, from Phenomenex (Torrance, Calif.); mobile phase A: 0.02% trifluoroacetic acid (TFA) in water; mobile phase B: 0.02% TFA in CH3CN, 10-95% B in 25 minutes (min.); flow rate: 1.0 mL/min; column temperature: 40° C.; detection wavelength: 254 and 215 nm) to provide 46 mg (50%) of the trifluoroacetic salt of 4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(piperazin-1-ylmethyl)-1-benzofuran-2-yl]nicotinonitrile 540 as an orange solid. HPLC retention time: 5.8 min.(g); MS: 463.3 (M+H); melting point: 113-115° C.; and HRMS: 463.2234.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by preparative HPLC (column: Prodigy ODS3, 4.6×150 mm, from Phenomenex (Torrance, Calif.); mobile phase A: 0.02% trifluoroacetic acid (TFA) in water; mobile phase B: 0.02% TFA in CH3CN, 10-95% B in 25 minutes (min.); flow rate: 1.0 mL/min; column temperature: 40° C.; detection wavelength: 254 and 215 nm)

Sources & evidence

ORD record
ord-c857581ebf8940b181ce9ceb8e197c60
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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