Trifluoroacetic acid → HCID 178448712, compound

HRID 720637Notes

Reaction equation

HRID 720637 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]4[N:28]=[CH:27][N:26](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:25]=4)=[O:23])=[CH:17][CH:16]=3)[NH:10][C:9]=2[C:8](=[O:48])[N:7]([CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[F:56])[C:6]1=[O:57])[CH2:2][CH2:3][CH3:4].[F:58][C:59]([F:64])([F:63])[C:60]([OH:62])=[O:61].C([SiH](CC)CC)C>ClCCl>[F:58][C:59]([F:64])([F:63])[C:60]([OH:62])=[O:61].[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([NH:21][C:22]([C:24]4[N:28]=[CH:27][NH:26][N:25]=4)=[O:23])=[CH:19][CH:20]=3)[NH:10][C:9]=2[C:8](=[O:48])[N:7]([CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[F:56])[C:6]1=[O:57])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 587392251-trityl-1H-[1,2,4]triazole-3-carboxylic acid {4-[3-butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide

Product 1

HCID 178448712HCID 178448712, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid {4-[3-butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide (15 mg, 0.02 mmol) in dichloromethane (1.0 mL) at 25° C. was treated with trifluoroacetic acid (1.0 mL). The resulting solution was stirred at 25° C. for 45 min. At this time, the reaction was treated with triethylsilane (0.003 mL, 0.02 mmol). This solution was stirred at 25° C. for 5 min and then was concentrated in vacuo. The resulting residue was purified by HPLC (20–90% acetonitrile/water (0.075% trifluoroacetic acid in both solvents) over 30 min). Fractions with the desired product were freeze dried to afford 1H-[1,2,4]triazole-3-carboxylic acid {4-[3-butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide; compound with trifluoro-acetic acid (4.5 mg, 40%) as a white, fluffy solid: EI-HRMS m/e calcd for C26H25N8O3F (M+) 516.2033, found 516.2027.

Workup

  1. stirringThis solution was stirred at 25° C. for 5 min
  2. concentrationwas concentrated in vacuo
  3. customThe resulting residue was purified by HPLC (20–90% acetonitrile/water (0.075% trifluoroacetic acid in both solvents) over 30 min)
  4. customdried

Sources & evidence

ORD record
ord-201db41299634a72ad3be5483a936182
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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